Br[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[N+:10]([O-:12])=[O:11].Cl.[CH3:14][C:15]1[S:16][C:17]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19][C:18]=2[N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:8][C:6]1[NH:5][C:4](=[O:9])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([N:21]2[CH2:22][CH2:23][C:17]3[S:16][C:15]([CH3:14])=[N:24][C:18]=3[CH2:19][CH2:20]2)[N:7]=1A suspension of 0.234 g (1.00 mmol) of the 6-bromo-2-methyl-5-nitro-3H-pyrimidin-4-one, 0.205 g (1.00 mmol) of the 2-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine hydrochloride and 0.304 g (2.20 mmol) of potassium carbonate in 2.0 ml of N,N-dimethylformamide was stirred at room temperature for 60 hours. The reaction mixture was then poured into 50 ml of an ice/water mixture and the crystals formed collected by filtration. Thus, a first crop of the 2-methyl-6-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-5-nitro-3H-pyrimidin-4-one was obtained. The mother liquor was then evaporated and the residue chromatographed on silica gel using a 9:1 v/v mixture of dichloromethane and methanol as eluent giving a second crop of the 2-methyl-6-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-5-nitro-3H-pyrimidin-4-one, in total 0.252 g (0.785 mmol, yield 78.5%) as light yellow solid; m.p. >200° C.; MS: [M+H]+=322.
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