Methyl iodide → HCID 53979775, compound

Participants

Reaction Steps

A mixture of 5-amino-3-(pent-2-ene-1-yl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione (350 mg, 1.35 mmol), NaH (80% dispersion in mineral oil, 42 mg, 1.4 mmol) and anhydrous DMF (15 mL) was protected from moisture and stirred at ambient temperature for 0.25 h. Iodomethane (0.1 mL, 1.61 mmol) was added and the mixture was stirred for an additional 1 h. The mixture was evaporated in vacuum and then H2O (20 mL) was added. The mixture was stirred for 15 min and then the solid was collected by filtration. The solid was suspended in MeOH (25 mL) and silica gel (5 g) was added. The mixture was evaporated and the dry powder was placed on top of a silica gel column (5.5×20 cm). The column was flash eluted with progressively increasing concentrations of MeOH in CH2Cl2 (%MeOH, vol in L): (0, 1); (1, 1); (2, 1); (3, 1). Eluate containing the homogeneous product was evaporated and the solid was dried in vacuum at 80° C. for 16 h; 240 mg (0.901 mmol, 66%), mp 184-187° C. Ir (KBr): ν3420, 3330 and 3210 (NH2), 1715 (C=O), and 1675 (C=N) cm-1. Uv, λmax (nm), (ε×10-3): pH 1, 300 (9.37), 252 (8.02), 222 (30.9); MeOH, 302 (9.07), 252 (8.35), 222 (31.3); pH 11, 300 (9.41), 252 (8.08), 226 (21.0). 1H nmr (DMSO-d6): δ0.954 (t, 3H, CH3), 2.15-2.22 (m, 2H, CH3CH2), 3.29 (s, 3H, CH3), 4.38 (d, 2H, NCH2), 5.34-5.40 (m, 1H, CHCH) 5.53-5.59 (m, 1H, CHCH), and 7.51 (br s, 2H, NH2). Anal. Calc'd for C11H14N4O2S (266.32): C, 49.61; H, 5.30; N, 21.04. Found: C, 49.93; H, 5.17; N, 20.77.

Provenance & Evidence