3,5-dimethyl-4-(3-morpholin-4-yl-propyl)-1H-pyrrole-2-carbaldehyde → 4-(3-Chloro-4-fluoro-phenylamino)-5-[3,5-dimethyl-4-(3-morpholin-4-YL-propyl)-1H-pyrrol-2-ylmethylene]-7-methyl-5,7-dihydro-pyrrolo [2,3-D]pyrimidin-6-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 4(3-chloro-4-fluoro-phenylamino)-7-methyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (100 mg, 0.34 mmol), 3,5dimethyl-4-(3-morpholin-4-yl-propyl)-1H-pyrrole-2-carbaldehyde (85 mg, 0.34 mmol) and piperidine (2 drops) in ethanol (3 mL) was stirred at 80° C. for 1 hour. The reaction was concentrated and column chromatographed to give 46 mg (26%) of the title compound as a light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 13.14 (br s, 1H, NH), 9.17 (s, 1H), 8.33 (s, 1H), 7.68 (m, 1H), 7.35 (s, 1H, H-vinyl), 7.32 (m, 2H), 3.55 (m, 4H, 2×CH2), 3.30 (s, 3H, CH3), 2.40 (m, 2H, CH2), 2.31 (s, 3H, CH3), 2.30 (m, 4H, 2×CH2), 2.20 (m, 2H, CH2), 2.10 (s, 3H, CH3), 1.55 (m, 2H, CH2).

Provenance & Evidence