tert-Butyldimethylsilyl chloride → HCID 10618349, compound

Participants

Reaction Steps

5-(2-Acetoxyethyl)-4-chloro-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidine 2.5 (750 mg, 1.66 mmol) was de-acetylated with methanol-aq ammonia (100 ml) and dried by co-evaporation with dry pyridine. The residue was dissolved in dry pyridine (80 ml) and tert-butyldimethylsilyl chloride (598 mg, 3.94 mmol) added. The solution was stirred overnight, evaporated, and residual pyridine removed by co-evaporation with water (2×20 ml). The residue was dissolved in chloroform (500 ml), washed with saturated aq. sodium bicarbonate solution (100 ml), dried (Na2SO4) and evaporated. The crude product was purified by silica gel chomatography (32×400 mm) eluting with chloroform to give a white solid, 826 mg, 88%. Rf (in C) 0.43; δH(d6-DMSO) 12.10 (1 H, br s, NH), 7.28 (1 H, s, 6-H), 3.81 (2 H, t J 7.0, O—CH2), 2.96 (2 H, t J 7.0, O—CH2CH2), 2.53 (3 H, s, CH3), 0.83 (9 H, s, 3×CH3), −0.05 (6 H, s, 2×CH3).

Provenance & Evidence