Category: 945-24-4

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.945-24-4, name is (2,4-Diaminopteridin-6-yl)methanol, molecular formula is C7H8N6O, molecular weight is 192.18, as common compound, the synthetic route is as follows.HPLC of Formula: C7H8N6O

2,4,5,6-Tetraminopyrimidine.H2SO4.H2O (75.0 g, 0.293 mole) was added to a stirred solution of BaCl2.2H2O (71.5 g, 0.293 mole) in H2O (1.45 l.) at 85-90 C. The mixture was stirred rapidly at about 90 C. for 15 min, cooled to 40 C., and filtered from BaSO4, which was washed thoroughly on a funnel with H2O. The clear, yellow filtrate was then diluted further with H2O to give a volume of 4.35 l. This solution of the tetraminopyrimidine.2HCl was then added to a solution of NaOAc (4.35 l. of 4 N) in which dihydroxyacetone (79.3 g, 0.88 mole) and cysteine.HCl.H2O (51.5 g, 0.293 mole) had just been dissolved. The resulting solution was stirred mechanically at room temperature while a slow stream of air was continuously passed through it for 26 hr. (Yellow-orange solid began separating after 2 hr.) The mixture was then kept in a refrigerator for 16 hr before the solid was collected, washed successively with cold H2O, EtOH, and Et2O before it was dried to constant weight in vacuo over P2O5 at 25 C. [The crude product mixture (47 g) was weighed in order to obtain an estimate of the volume of 48% HBr required to form hydrobromide salts.] A mechanically stirred mixture of the dried solid and EtOH (6.05 l.) was heated to 70 C., and a solution of 48% HBr (28 ml) in EtOH (490 ml) was added in a thin stream while the mixture was maintained at 70-75 C. The mixture was then refluxed for about 5 min with rapid stirring while nearly all of the solid dissolved. The hot solution was treated with Norit and filtered through a Celite mat. The clear yellow filtrate was kept in a refrigerator overnight while a first crop of orange-colored solid separated. The collected solid was washed with EtOH, then dried in vacuo (56 C. over P2O5) to give 17.2 g of product. The filtrate was concentrated by evaporation (rotary evaporator, H2O aspirator, bath to 35 C.) to about 2 l. and then refrigerated to give a second crop, which was dried as before, of 10.2 g; total yield 27.4 g (34%). The 1H NMR spectrum of this material in CF3CO2D showed it to contain a barely detectable amount of methyl substituted 2,4-diaminopteridine.HBr as evidenced by very weak signals at 62.83 (CH3) and 68.85 (pteridine ring H). Strong signals produced by the desired product occur at delta5.28 (6-CH2O) and 69.08 (C7-H). The proportion of desired product to the methyl-substituted contaminant was estimated from the 1H NMR integrals to be 20:1. The 1H NMR spectrum also revealed retention of a small amount of EtOH in the product dried as described but not enough to interfere with the conversion of it to 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,945-24-4, (2,4-Diaminopteridin-6-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Kamen, Barton; Cole, Peter; Smith, Angela; Zebala, John A.; US2005/209239; (2005); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 945-24-4, name is (2,4-Diaminopteridin-6-yl)methanol. A new synthetic method of this compound is introduced below., Formula: C7H8N6O

To a solution of triphenylphosphene (408 mg, 1 .03 mmol) in anhydrous DMA ( 1 mL) is added bromine dropwise at 0 0C (0.08 mL, 1 .03 mmol) under N2 atmosphere. After stirring for 5 additional minutes, (2,4-diaminopteridin-6-yl)methanol (100 mg, 0.33 mmol) is added at once and the reaction mixture is stirred at RT for 18 h. Barium oxide ( 100 mg, 0.65 mmol) is then added to the reaction mixture followed by 3-aminobenzoic acid (107 mg, 0.78 mmol) at RT. The reaction mixture is then heated at 56 0C and stirred at that temperature for 24 h and cooled to RT. The mixture is diluted with methylene chloride (5 mL) and the resulting brownish precipitate is filtered. The solids are washed with water and methanol. The solids are then taken in methanol and heated at reflux for 2 h. After cooling to RT, the solids are filtered again and dried overnight in a heated vacuum oven to give 45 mg product (Yield: 26.9%) as a brownish yellow solid. 1 H NMR (500 MHz, DMSOd6) delta 4.6 (br s, 2H), 6.7 (s, 1 H), 6.9-7.0 (d, 1 H), 7.15-7.3 (m, 2H), 7.38 (br s, 2H), 8.6-8.7 (br s, I H), 8.9 (s, I H), 9.3-9.4 (m, 2H), 12.8 (br s, I H); LC-MS m/z 312 (MH+), retention time 1 1 .48 min., HPLC Method B.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 945-24-4, (2,4-Diaminopteridin-6-yl)methanol.

Reference:
Patent; BIORELIX, INC.; COISH, Philip, D., G.; WICKENS, Phil; DIXON, Brian; OSTERMAN, David; KHIRE, Uday, R.; NAVIA, Manuel; BERMAN, Judd; KAUR, Harpreet; WILSON, Jeffrey; UNDERWOOD, Dennis; WO2010/110907; (2010); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 945-24-4, name is (2,4-Diaminopteridin-6-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H8N6O

2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride (4.40 g, 19.2 mmol) was dissolved in hot water (150 mL) and after cooling to 21 C the solution was neutralized with 1M NaOH aq. solution to pH 7 (ca. 20 mL) . The formed precipitates were collected by filtration, washed with water, and dried in vacuo over P205 to afford an orange-beige solid corresponding to 2,4-diamino-6- (hydroxymethyl)pteridine. The solid was suspended in dry DMAc (25 mL) and triphenylphosphine dibromide ( 18.1 g, 42.9 mmol) was added to the suspension. The turbid and dark mixture was stirred for 24 h at 20 C under a N2 atmosphere. Then 4-aminobenzoic acid (2.97 g, 19.6 mmol) was added to the reaction and stirred for 3 additional days. The reaction mixture was poured into 250 mL of 0.33M NaOH and the precipitate was filtered off. The filtrate was neutralized with 10% aq . acetic acid (ca. 20 mL and the precipitate form upon neutralization was filtered, washed with water, triturated with MeOH, filtered, and dried in vacuo to afford 7 as an orange-beige solid (5.70 g, 91%) . XH NMR (400 MHz, DMSO-d5) delta 12.15 (br s, 1H), 8.63 (s, 1H), 8.17 (br s, 1H), 7.94 (br s, 1H), 7.73 (d, J = 9.0 Hz, 2H), 7.04 (br s, 2H), 6.83 (d, J = 9.0 Hz, 2H), 4.81 (s, 2H), 3.23 (s, 3H); 13C NMR (101 MHz, DMSO-d5) delta 167.8, 163.2, 161.1, 152.3, 149.5, 147.8, 131.5, 122.2, 118.1, 111.7, 100.0, 55.2, 39.6.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 945-24-4, (2,4-Diaminopteridin-6-yl)methanol.

Reference:
Patent; DANMARKS TEKNISKE UNIVERSITET; PEIRO CADAHIA, Jorge; CLAUSEN, Mads, Hartvig; BONDEBJERG, Jon; HANSEN, Christian, Abildgaard; (101 pag.)WO2018/37120; (2018); A1;,
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