Triethylsilane → 2-(6-Cyano-1H-benzimidazol-1-yl)-5-nitropyrimidin-4-yl thiocyanate

Participants

Reaction Steps

To a solution of 0.58 g (1.25 mmol) 4-(2,4-dimethoxybenzylamino)-3-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)benzonitrile in 10 mL 30% (v/v) TFA in DCM was added 0.01 mL of triethylsilane. The mixture was stirred for 0.5 hr, LCMS indicated the completion of de-protection. A red residue was obtained after removing the volatiles on rotary evaporator, and was suspended (majority dissolved) in 10 mL 1:1 trimethyl orthoformate:MeOH. The resulting mixture was stirred for 2 hrs at room temperature. Yellow solids were precipitated. Desired product (0.38 g, ˜95% overall yield) was obtained after suction filtration and washing with cold MeOH twice. 1H-NMR (300 MHz, CDCl3+10% CD3OD) δ 9.5 (s, 1H), 9.2 (s, 1H), 9.1 (s, 1H), 7.9 (d, 1H), 7.7 (d, 1H) ppm; MS (ESI), m/z 324 ([M+H]+).

Provenance & Evidence