Trimethylsilyl iodide → HCID 25155122, compound

Participants

Reaction Steps

At 0° C., iodotrimethylsilane (12.3 mg, 0.06 mmol) was added slowly to a solution of 8-[5-chloro-4-(2-methylcarbamoyl-phenylamino)-pyrimidin-2-ylamino]-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester (25 mg, 0.04 mmol) in methylene chloride (5 mL). The mixture solution was warmed to room temperature and stirred for 1 hour. The mixture was quenched with a few drops of methanol, stirred for 10 minutes and concentrated. The residue was treated with 1N HCl (0.5 mL), and then made basic (pH 10) with potassium carbonate. The mixture was extracted with methylene chloride and chloroform, and then dried over sodium sulfate. Chromatography of the crude solid with preparative TLC using methylene chloride and methanol (25:1) gave 6.3 mg of 2-[5-chloro-2-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide (33%): 1H NMR (300 MHz, CDCl3) δ 8.45 (d, 1H), 8.05 (s, 1H), 7.6 (q, 2H), 7.43 (t, 2H), 7.3 (dd, 1H), 7.13 (d, 2H), 4.0 (s, 2H), 3.43 (s, 2H), 2.92 (s, 3H); MS (m/e): 438.3 (M+1).

Provenance & Evidence