Diisobutylaluminumhydride → (R)-2-((5-Bromo-2-chloropyrimidin-4-yl)amino)propanal

Participants

Reaction Steps

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.

Provenance & Evidence