Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:13].[CH3:14][NH:15][CH3:16].C1COCC1.C(N(C(C)C)CC)(C)C>O1CCOCC1.O>[CH3:14][N:15]([CH3:16])[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:13]To a solution of ethyl 6-chloro-5-methylpyrimidine-4-carboxylate (35) (0.9 g, 4.48 mmol) dissolved in dioxane (20 ml) were added dimethyl amine in THF (1M. 22.43 ml, 22.43 mmol) and diisopropyl ethylamine (3 ml, 22.43 mmol). The reaction mixture was heated to 80° C. for 16 h. Then the mixture is cooled to room temperature, diluted with water, and extracted with EtOAc (2×50 mL). The combined organic layer was washed with water, brine, dried over sodium sulfate, and concentrated at reduced pressure to yield ethyl 6-(dimethylamino)-5-methylpyrimidine-4-carboxylate (23) as a light yellow liquid; 0.4 g (43%).
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