Hydrochloric Acid → HCID 11965379, compound

Participants

Reaction Steps

To a solution of N-(2,4-dioxo-6-propionyl-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (50 mg, 0.132 mmol) in THF (1 mL) and MeOH (1 mL) was added sodium borohydride (80 mg, 2.11 mmol). The resultant mixture was stirred for 20 h. After that time, it was then diluted with EtOAc and water and the pH was adjusted to 4-5 with an aqueous hydrochloric acid solution (1N). The organic phase was separated and washed once with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the crude product by flash chromatography (silica gel 60, DCM/MeOH 100:0→90:10) to afford N-[6-(1-hydroxy-propyl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (39 mg, 0.102 mmol, 78%) as a white powder, m.p. 219-222° C., 1H-NMR (DMSO-d6, 400 MHz) 11.93 (br s, 1H), 10.38 (br s, 1H), 8.33 (s, 1H), 7.50 (s, 1H), 5.63 (m, 1H), 5.27 (m, 1H), 3.17 (s, 3H), 1.60 (m, 2H), 0.93 (m, 3H).

Provenance & Evidence