Dimethyl Sulfoxide → 4-Ethoxy-2-methylamino-quinazoline-6-carbaldehyde

Participants

Reaction Steps

To a combined solution of acetonitrile (40 mL) and DMSO (40 mL) was added tetrakis(triphenylphosphine)palladium(0) (1.65 g, 1.43 mmol), anhydrous sodium formate (5.82 g, 85.6 mmol) followed by powder (6-bromo-4-ethoxy-quinazolin-2-yl)-methyl-amine (4 g, 14.3 mmol) and the resultant mixture was heated to 85° C., 50 psi under CO atmosphere. After being stirred for 48 hours, the cooled mixture was poured to water and extracted with DCM (3×200 mL). The combined organic phase was washed with brine, dried over Na2SO4, evaporated to give a brown solid which was purified by column to afford 4-ethoxy-2-methylamino-quinazoline-6-carbaldehyde (1 g, 4.3 mmol, 30%) as a pale solid. 1H NMR (DMSO-d6): δ 9.95 (s, 1H), 8.38 (s, 1H), 8.00-7.97 (d, 1H), 7.59-7.56 (m, 1H), 7.46-7.44 (d, 1H), 4.53-4.48 (q, 2H), 2.89-2.87 (d, 3H), 1.44-1.40 (t, 3H).

Provenance & Evidence