Methanol → 2,4-Diamino-5-propylpyrido[2,3-d]pyrimidine-6-methanol

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Reaction Steps

2,4-Diamino-5-propylpyrido [2,3-d]pyrimidine-6-carboxaldehyde (95 mg, 0.41 mmol) was stirred with MeOH (20 mL), and the near-solution was treated with 3 portions of NaBH4 (17 mg total, 0.45 mmol) added at 15-min intervals. Complete solution occurred after the first addition of NaBH4. The solution was left at 20°-25° C. for 1 hour. The solution was treated with H2O (1 mL), neutralized to pH 7 with glacial AcOH, and evaporated to near dryness. Solid residue was stirred with a little cold H2O (~1 mL), collected, and dried to give a first crop of 6-hydroxymethyl compound (III-1, where R1 is propyl); yield 31% (30 mg). The filtrate from this compound was evaporated to dryness, and the residue was extracted several times with boiling EtOAc to provide additional product (80 mg).

Provenance & Evidence