Acetic Anhydride → HCID 60036691, compound

Participants

Reaction Steps

4-(3-chloro-2-fluoroanilino)-6-[(3R)-pyrrolidin-3-yloxy]-7-methoxyquinazoline (0.22 g, 0.51 mmole) (prepared as described in Example 29-preparation of starting materials) was dissolved in a mixture of methylene chloride (4 ml), pyridine (1 ml) and diisopropylethylamine (0.17 ml) under a nitrogen atmosphere. Acetic anhydride (0.1 ml, 1.0 mmole) was added and the mixture stirred at ambient temperature for 3 hours. The mixture was then partitioned between saturated aqueous NaHCO3 and ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography eluting with methylene chloride/methanol (saturated with ammonia) (96/4). The fractions containing the expected product were evaporated and triturated with diethylether. The solid was filtered and dried under vacuum to give the title product as a white solid (0.12 g: 55%); 1H NMR Spectrum: (DMSO d6) 1.95-1.98 (m, 3H); 2.14-2.40 (m, 2H); 3.53-3.70 (m, 3H); 3.91 (m, 4H); 5.12-5.21 (m, 1H); 7.15-7.30 (m, 2H); 7.4-7.60 (m, 2H); 7.70-7.90 (m, 1H); 8.36-8.37 (d, 1H); 9.60-9.62 (m, 1H); Mass Spectrum: (M+H)+ 431.

Provenance & Evidence