Water → HCID 18186495, compound

Participants

Reaction Steps

Triethylsilane (0.14 ml, 1.10 mmol) was added to a solution of 4-anilino-2-chloro-5-[1-hydroxy-1-phenylmethyl]pyrimidine (Method 58; 170 mg, 0.55 mmol) in trifluoroacetic acid (1.5 ml), and the mixture was stirred for 64 hours. Water (20 ml) was added and the mixture was neutralised with sodium carbonate powder and extracted with DCM (3×20 ml). The extracts were combined, washed with water (30 ml), dried, concentrated to a volume of 5 ml, and loaded on a Varian Mega Bond Elut column. Elution with DCM and concentration of the appropriate fractions gave the product as a yellow crystalline solid (42 mg, 26%). NMR (CDCl3): 3.93 (s, 2H), 6.45 (br s, 1H), 7.08 (m, 1H), 7.2-7.4 (m, 9H), 8.09 (s, 1H); MS (MH+): 296.2, 298.2.

Provenance & Evidence