反应详情

A solution of 40.0 g (135.8 mmol) of methyl-N-(5-bromo-2-chloropyrimidin-4-yl)-D-alaninate in 800 ml of toluene is mixed at −78° C. with 310 ml of a 1.2 molar solution of diisobutyl aluminum hydride. After 30 minutes, it is carefully quenched with methanol. The batch is heated to room temperature and diluted with 1000 ml of tert-butyl methyl ether. It is washed successively with 1N HCl (3×100 ml), saturated sodium bicarbonate solution (3×) and saturated NaCl solution (3×). The organic phase is dried (MgSO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate: 4:1-1:1). 22.5 g (83.9 mmol, corresponding to 62% of theory) of the product is obtained.

1. customit is carefully quenched with methanol
2. additiondiluted with 1000 ml of tert-butyl methyl ether
3. washIt is washed successively with 1N HCl (3×100 ml), saturated sodium bicarbonate solution (3×) and saturated NaCl solution (3×)
4. dry with materialThe organic phase is dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated by evaporation
7. customThe remaining residue is purified by chromatography (hexane/ethyl acetate: 4:1-1:1)
8. custom22.5 g (83.9 mmol, corresponding to 62% of theory) of the product is obtained