Sodium borohydride → HCID 178470043, compound

Participants

Reaction Steps

To a solution of ethyl 2-(1-(benzyloxycarbonylamino)-4-oxocyclohexyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (1.5 g, 3.5 mmol) in methanol (35 mL) at room temperature was added NaBH4 (138 mg, 3.66 mol) and the resulting mixture was stirred for 1 h. Methanol was then removed under reduced pressure and the mixture was diluted with CH2Cl2 (200 mL), washed with 1N HCl (100 mL) followed by brine (100 mL). The organic fraction was dried (Na2SO4), filtered and concentrated to afford the title compound as a light yellow solid (1.3 g, 86% yield). 1H NMR (500 MHz, DMSO-D6) δ: 12.46 (s, 1H), 10.24 (s, 1H), 7.31-7.35 (m, 5H), 7.11 (brs, 1H), 4.28-4.32 (m, 2H), 4.29 (q, 2H, J=7.22 Hz), 3.43-3.46 (m, 1H), 2.31-2.33 (m, 1H), 2.15-2.22 (m, 2H), 1.77-1.83 (m, 2H), 1.65-1.67 (m, 2H), 1.44-1.49 (m, 2H), 1.28 (t, 3H, J=7.22 Hz). LCMS (M+H)=432.37.

Provenance & Evidence