6-(4-Methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine → 4-(2-(2-Methylpyrimidin-5-yl)-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine

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Reaction Steps

To a solution of 6-(4-methanesulfonyl-piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (100 mg) in 1,2-dimethoxyethane (10 mL) was added 2-methyl-5-tributylstannanyl-pyrimidine (176 mg) and copper(I)bromide-dimethyl sulfide (94 mg) and the reaction mixture was stirred at room temperature for 10 minutes. Tetrakis(triphenylphosphine)palladium (0) (13 mg) was then added and the reaction mixture was heated at reflux for 16 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (20 mL) and washed with water (2×20 mL) and brine (2×20 mL). The organic phase was dried (MgSO4), reduced in vacuo and purified by column chromatography to give 306. NMR: (CDCl3) 2.69-2.72 (4 H, m), 2.83 (3 H, s, Me), 2.84 (3 H, s, Me), 3.31-3.34 (4 H, m), 3.90-3.93 (6 H, m), 4.06-4.08 (4 H, m), 7.37 (1 H, Ar) and 9.58 (1 H, Ar). MS: (ESI+): MH+=490.15

Provenance & Evidence