[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:24]N(C)C=O.CI.O>[Cl-].[Na+].O.C(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[N:7]([CH3:24])[C:8]1[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]To a solution of 1.9 g (5.73 mmol) (2-methylsulfanyl-4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert.-butyl ester in 15 ml N,N-dimethylformamide 0.29 g (7.45 mmol) sodiumhydride (60% dispersion in mineraloil) was added and the reaction mixture stirred for 1 hr. After the addition of 0.57ml (9.17 mmol) methyl iodide at 0°, the reaction mixture was stirred for 3 hrs. The reaction mixture was distributed between 75 ml H2O, 75 ml brine and 75 ml CH2Cl2. The phases were separated, the aqueous layer washed twice with 75 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 15:1) to give 1.95 g (98%) methyl-(2-methylsulfanyl-4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert.-butyl ester as a colorless oil. MS (TSP): 345 (M+).
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