反应详情

To a stirred solution of 2-(3-phenyl-pyridin-2-yl)-acetamidine (162) (300 mg, 1.10 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester (4) (511 mg, 1.66 mmol) in methanol (5 mL) was added sodium methoxide (1.3 mL, 3.32 mmol) at 0° C., then the reaction mixture was allowed to warm to room temperature, stirred for 16 h. Silica thin layer chromatography was performed (50% ethyl acetate in hexane, Rf=0.3). After completion of the reaction, it was quenched with water, methanol was evaporated and water (30 mL) was added. The mixture was extracted with ethyl acetate (3×30 mL) and the separated organic part was dried and concentrated to get a crude product, which was purified by a CombiFlash column (eluted at 90% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(3-phenyl-pyridin-2-ylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (163) (250 mg, 48.1%) as a yellow sticky product.

1. customAfter completion of the reaction, it
2. customwas quenched with water, methanol
3. customwas evaporated
4. additionwater (30 mL) was added
5. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
6. customthe separated organic part was dried
7. concentrationconcentrated
8. customto get a crude product, which
9. customwas purified by a CombiFlash column (eluted at 90% ethyl acetate in hexane)