Sodium borohydride → HCID 89579764, compound

Participants

Reaction Steps

2-Methylsulphonyl-5-phenyl-4 [4-2-pyrrolidin-1-ylethoxymethyl-1-piperidyl]furo[2,3-d]-pyrimidine pyrimidine (75 mg, 0.15 mmol) in ethanol (5.0 mL) was treated with sodium borohydride (15 mg, 0.38 mmol) at 20° C. with continuous stirring for 30 min. A further 30 mg of sodium borohydride was added and the reaction was stirred at 20° C. for a further 1 h. A further 60 mg of sodium borohydride was added and the reaction was stirred at 20° C. for a further 1 hr then concentrated in vacuum to a gum and the residue partitioned between dichloromethane and water. The dichloromethane layer was separated, dried over sodium sulphate and concentrated in vacuum to a gum. The gum was purified by preparative HPLC to give 5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]furo[2,3-d]pyrimidine (53 mg, 0.13 mmol, 84%). 1H NMR (CDCl3) δ: 1.02 (2H, m), 1.5 (2H, m), 1.75 (6H, m), 2.45-2.8 (9H, m), 3.2 (2H, d, J=8 Hz), 3.5 (2H, t, J=8 Hz), 3.95 (2H, d, J=12 Hz), 7.35-7.45 (5H, m), 7.52 (1H, s), 8.45 (1H, s). LCMS RT=5.14 min. M+1=407.

Provenance & Evidence