[CH2:1]([N:4]=[C:5]([NH2:15])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=1)[CH2:2][CH3:3].I([O-])(=O)(=O)=[O:17].[Na+].CCOC(C)=O.CO>CO.O>[CH2:1]([N:4]=[C:5]([NH2:15])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13]([CH3:14])=[O:17])[N:8]=1)[CH2:2][CH3:3]A solution of 4-(2-propylguanidino)-2-methylthiopyrimidine (1.6 g.) in MeOH (25 ml.) was heated on a steam bath while a solution of sodium metaperiodate (1.6 g.) in water (15 ml.) was added dropwise over 15 minutes. Further sodium metaperiodate in water (10% w/v) was added until analysis by t.l.c. on silica using EtOAc/MeOH 4:1 v/v as eluant showed absence of starting material. The reaction mixture was evaporated in vacuo, and the residue partitioned between methylene chloride and water. The organic phase was worked up to give 4-(2-propylguanidino)-2-methylsulphinylpyrimidine, m.p. 179°-180°.
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