3-methyl-5-(4-methylpiperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde → 4-(3-Chloro-4-fluoro-phenylamino)-7-methyl-5-[3-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrol-2-yl-methylene]-5,7-dihydro-pyrrolo[2,3-D]pyrimidin-6-one

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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 (80 mg, 0.27 mmol), 3-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde (1.2 equiv.) and piperidine (1 drop) in ethanol (2 mL) was stirred at 90° C. for 2 hours. The reaction was diluted with water and the precipitate was collected by vacuum filtration, washed with water, ethyl acetate and hexane and dried to give 120.5 mg (72%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 13.42 (br s, 1H, NH), 9.32 (br s, 1H), 8.40 (s, 1H), 7.71 (m, 1H), 7.35-7.41 (m, 3H), 6.60 (s, 1H), 3.69 (m, 4H, 2×CH2), 3.30 (s, 3H, CH3), 2.35 (m, 4H, 2×CH2), 2.21 (s, 3H, CH3),2.20 (s, 3H, CH3). MS 510 [M+1].

Provenance & Evidence