Sodium Hydroxide → 2-Chloro-4-((cyclopropylmethoxy)methyl)-6-(1-ethoxyvinyl)pyrimidine

Participants

Reaction Steps

Cyclopropylmethanol (0.368 mL, 4.66 mmol) and sodium hydroxide (aq, 5M, 0.70 mL, 3.50 mmol) were added to a solution of (2-chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate (682 mg, 2.33 mmol) in benzene (8 mL). Tetrabutylammonium hydrogen sulfate was added (79 mg, 0.23 mmol). The mixture was stirred vigorously at rt over night. The organic phase was filtered through a short silica plug which was washed with 10% MeOH in EtOAc (75 mL) and the solvents were evaporated. The residue was purified by preparative HPLC to give the title compound 88 mg (14%).

Provenance & Evidence