[C:1]([C:3](=[C:13]([S:16][CH3:17])SC)[C:4]([C:6]1[O:10][C:9]([C:11]#[N:12])=[CH:8][CH:7]=1)=O)#[N:2].[N+]([O-])(O)=O.[NH2:22][C:23]([NH2:25])=[NH:24].C(N(CC)CC)C.O>CN(C=O)C>[NH2:25][C:23]1[N:24]=[C:4]([C:6]2[O:10][C:9]([C:11]#[N:12])=[CH:8][CH:7]=2)[C:3]([C:1]#[N:2])=[C:13]([S:16][CH3:17])[N:22]=1
Following the method of Rudorf and Augustin (J. Prakt. Chem. 1978, 320, 576), a solution of 300 mg (1.13 mmol) 5-(2-cyano-3,3-bis-methylsulfanyl-acryloyl)-furan-2-carbonitrile, 166 mg (1,36 mmol) guanidine nitrate and 0.40 ml (2.84 mmol) triethylamine in 5 ml DMF was heated at reflux for 1 h. The reaction mixture was then cooled to room temperature and poured onto 250 ml water, extracted three times with ethyl acetate, and the combined organic phases dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate) afforded 120 mg (41%) 2-amino-4-(5-cyano-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a light yellow crystalline solid. ES-MS m/e (%): 256 ([M—H]−, 100).
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