[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10](Br)=[CH:11][CH:12]=2)[C:5]([C:14]#[N:15])=[C:4]([S:16][CH3:17])[N:3]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH2:44]([OH:46])[CH3:45].CN([CH:50]=[O:51])C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:44]([O:46][C:50]([C:10]1[O:9][C:8]([C:6]2[C:5]([C:14]#[N:15])=[C:4]([S:16][CH3:17])[N:3]=[C:2]([NH2:1])[N:7]=2)=[CH:12][CH:11]=1)=[O:51])[CH3:45]To a stirred solution of 1.17 g (3.74 mmol) 2-amino-4-(5-bromo-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile in 15 ml DMF at room temperature were added 343 mg (0.37 mmol) tris(dibenzylideneacetone)dipalladium(O) and 287 mg (0.94 mmol) triphenylarsine. Carbon monoxide was bubbled through the reaction mixture for 10 min, then 2.61 ml (18.7 mmol) triethylamine and 10.9 ml (187 mmol) ethanol were added. The reaction mixture was then heated at 90° C. for 16 hours under a carbon monoxide atmosphere (balloon). The reaction mixture was then concentrated in vacuo. Flash chromatography (1/1 ethyl acetate/hexane then ethyl acetate) afforded 70 mg (6%) 5-(2-amino-5-cyano-6-methylsulfanyl-pyrimidin-4-yl)-furan-2-carboxylic acid ethyl ester as a yellow crystalline solid. EI-MS m/e (%): 304 (M+, 95), 303 ([M—H]+, 100), 275 (32), 259 (93), 231 (72), 202 (32).
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