Isopropanol → HCID 13374342, compound
Reaction equation
[Na].[Cl:2][C:3]1[N:8]=[C:7](Cl)[C:6]([CH2:10][C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[CH:5][N:4]=1.[CH:18]([OH:21])([CH3:20])[CH3:19]>>[Cl:2][C:3]1[N:8]=[C:7]([O:21][CH:18]([CH3:20])[CH3:19])[C:6]([CH2:10][C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[CH:5][N:4]=1Participants
4
Procedure
A solution of 1.38 g (0.06 g-atom) of sodium metal in 25 ml of isopropanol was heated to reflux until complete dissolution of the metal. The alkoxide solution was cooled to -10° and treated dropwise with a solution of 15.0 g (60 mmol) of 2,4-dichloro-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine prepared as in Example 1 in 60 ml of isopropanol. The resulting mixture was allowed to warm to room temperature over 18 hours and was then concentrated. The resulting oil was dissolved in ethyl acetate, filtered, washed with water, dried over magnesium sulfate, filtered, concentrated and dried under vacuum to give 14.5 g (0.052 mol, 87%) of 2-chloro-4-isopropoxy-5-[(6-methyl-3-pyridinyl)methyl]pyrimidine. Recrystallization from ethyl acetate and petroleum ether gave yellow crystals: m.p. 38°-42°.