O[C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[CH:4][N:3]=1.[ClH:11].[CH3:12][NH:13][CH3:14].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C.S(Cl)(Cl)=O.C(Cl)Cl.O>[Cl:11][C:2]1[C:7]([C:8]([N:13]([CH3:14])[CH3:12])=[O:10])=[CH:6][N:5]=[CH:4][N:3]=1
A mixture of 4-hydroxy-5-pyrimidinecarboxylic acid (0.88 g, 6.3 mmol) in 5 drops of DMF and 6 mL of thionyl chloride was heated at reflux for 3 hours. The mixture was concentrated and the residue was dissolved in methylene chloride. A mixture of the residue, dimethylamine hydrochloride (0.62 g, 7.6 mmol) and triethylamine (4.5 mL, 31.5 mmol) in 50 mL of methylene chloride was stirred at 0° C. for 0.5 hours. The mixture was poured into water and aqueous sodium bicarbonate. The mixture was extracted with methylene chloride (2×30 mL) and the extract was washed with brine, dried (Na2SO4) and concentrated by rotary evaporation to give 4-chloro-N,N-dimethyl-5-pyrimidinecarboxamide (0.66 g, 3.6 mmol) as an oil.
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