Sodium ethoxide → HCID 57780694, compound

Participants

Reaction Steps

To a solution of methanesulfonic acid 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-5,6,7,8-tetrahydro-quinazolin-8-yl ester (86 mg, 0.2 mmol) in methanol (2 mL) was added sodium ethanolate (17 mg, 0.3 mmol). The reaction was stirred at room temperature over night under nitrogen, heated to reflux for 1 hour. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified by reversed phase preparative HPLC using a mixture of water containing formic acid and acetonitrile to yield the title compound (23 mg, 28%) as a yellow gum. MS ISP (m/e): 366.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.35 (s, 1H), 8.26 (s, 1H), 7.85 (d, 1H), 7.75 (s, 1H), 7.16 (d, 1H), 7.09 (d, 1H), 6.88 (s, 1H), 4.19 (t, 1H), 3.88 (s, 3H), 3.58 (s, 3H), 2.55-2.80 (m, 2H), 2.33 (s, 3H), 2.15 (m, 1H), 1.72-2.05 (m, 3H).

Provenance & Evidence