Acetic Acid → HCID 46199744, compound

Participants

Reaction Steps

(R)-N2-(4-(Oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (135 mg, 0.34 mmol, example 80a) was dissolved in methanol (3 mL). Acetic acid (0.020 mL, 0.34 mmol) was added followed by formaldehyde (0.026 mL, 0.34 mmol). The reaction mixture was stirred at room temperature for 15 minutes and sodium cyanoborohydride (21.62 mg, 0.34 mmol) MP—CNBH3 was added. The reaction was stirred overnight, the MP—CNBH3 was filtered off and the solvent was evaporated under reduced pressure. The crude was dissolved in methanol, filtered and purified by HPLC yielding (R)-6-methyl-N2-(4-(oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (46.0 mg, 30.3%). MS (ES+) m/z 407.2 (M+H)+

Provenance & Evidence