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With N-Bromosuccinimide; lithium diisopropyl amide In tetrahydrofuran; cyclohexane; ethyl acetate
A solution of lithium diisopropyl amide (3.0 mL of a 1.5 M solution in cyclohexane) in THF (7 mL) under N2 was cooled to -78° C. To the cooled solution was added a solution 4-methoxy[3,2-d]pyrimidine (85, 0.55 g, 3.3 mmol) in THF (8 mL) via canula. The resulting suspension was stirred at -78° C. for 30 min and then a solution of N-bromosuccinimide (0.96 g, 5.4 mmol) in THF (10 mL) was added via canula. The cooling bath was removed, the reaction mixture stirred at room temperature for 12 hours, and then diluted with 50 mL water. The aqueous mixture was extracted with ethyl acetate. The organic layer was washed with water followed by saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent evaporated under reduced pressure. Purification by column chromatography on silica gel with 10percent ethyl acetate/hexane as eluant yielded 6-bromo-4-methoxy[3,2-d]pyrimidine (0.61 g, 75percent yield) as a white solid. 6-(3-Thienyl)-4-methoxy[3,2-d]pyrimidine (215).
6-(thien-3-yl)-4-methoxy[3,2-d]pyrimidine[ No CAS ]
[ 69543-97-1 ]
Yield
Reaction Conditions
Operation in experiment
75%
With N-Bromosuccinimide; lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; ethyl acetate;
A solution of lithium diisopropyl amide (3.0 mL of a 1.5 M solution in cyclohexane) in THF (7 mL) under N2 was cooled to -78 C. To the cooled solution was added a solution 4-methoxy[3,2-d]pyrimidine (85, 0.55 g, 3.3 mmol) in THF (8 mL) via canula. The resulting suspension was stirred at -78 C. for 30 min and then a solution of N-bromosuccinimide (0.96 g, 5.4 mmol) in THF (10 mL) was added via canula. The cooling bath was removed, the reaction mixture stirred at room temperature for 12 hours, and then diluted with 50 mL water. The aqueous mixture was extracted with ethyl acetate. The organic layer was washed with water followed by saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent evaporated under reduced pressure. Purification by column chromatography on silica gel with 10% ethyl acetate/hexane as eluant yielded 6-bromo-4-methoxy[3,2-d]pyrimidine (0.61 g, 75% yield) as a white solid. 6-(3-Thienyl)-4-methoxy[3,2-d]pyrimidine (215).
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