Application of 14631-08-4 , The common heterocyclic compound, 14631-08-4, name is 2-Chloropyrimidine-4,5-diamine, molecular formula is C4H5ClN4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
DIPEA (0.35 mL, 2.03 mmol) was added to a stirred suspension of 2-chloro-4,5- diaminopyrimidine (100 mg, 0.69 mmol), trans-(2S)-2-(tert-butoxycarbonylamino)-2-(4- methylcyclohexyl)acetic acid (271 mg, 0.99 mmol) and HATU (410 mg, 1.08 mmol) in DCM (5 mL) at 20C. The reaction mixture was stirred at 20C for 18 h, then diluted with DCM (15 mL) and washed with saturated aqueous NaHCO3 solution (10 mL). The organic layer was filtered through a hydrophobic frit, and the solvent was concentrated in vacuo. The resulting dark brown oil was dissolved in EtOH (10 mL), and K2CO3 (398 mg, 2.88 mmol) was added. The suspension was heated at 80C in a sealed vial for 40 h. After cooling, the mixture was diluted with water (10 mL), and the aqueous layer was extracted with DCM (3 x 15 mL). The combined organic extracts were filtered through a hydrophobic frit, and the solvent was concentrated in vacuo. The resultant dark brown oil was separated by flash column chromatography, eluting with EtOAc/heptane (0-50% gradient), to afford the title compound (80 mg, 30%) as a yellow oil that slowly solidified on standing. dH (250 MHz, CDCl3) 11.73 (br s, 1H), 8.90 (s, 1H), 5.87-5.64 (m, 1H), 4.74-4.62 (m, 1H), 1.75-1.68 (m, 4H), 1.41 (s, 9H), 1.28-1.04 (m, 6H), 0.88-0.84 (m, 3H). LCMS (Method 10): [M+H]+ m/z 380 and 382, RT 1.18 minutes.
The synthetic route of 14631-08-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; FOULKES, Gregory; FROST, James Richard; HORSLEY, Helen Tracey; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; REUBERSON, James Thomas; SCHULZE, Monika-Sarah Elisabeth Dorothea; TAYLOR, Richard David; YAU, Wei Tsung; ZHU, Zhaoning; (246 pag.)WO2019/138017; (2019); A1;,
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