[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[N:13]=[C:12]([NH2:14])[CH:11]=[N:10][C:9]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][N:16]=1.[C:21](Cl)(=[O:23])[CH3:22]>CN(C=O)C.C(OCC)(=O)C>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[N:13]=[C:12]([NH:14][C:21](=[O:23])[CH3:22])[CH:11]=[N:10][C:9]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][N:16]=1Sodium hydride (42 mg, 1.05 mmol) was added to a stirred solution of 6-(2-furyl)-5-pyrimidin-4-ylpyrazin-2-amine (Example 8, 100 mg, 0.42 mmol) in DMF (4 mL) at 0° C. under nitrogen. The solution was allowed to stir for 30 min. at 0° C. Acetyl chloride (60.0 μL, 0.84 mmol) was then added and the reaction mixture was warmed up to room temperature and stirred for 3 days. The reaction was diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by silica gel flash chromatography (50% ethyl acetate in hexanes to 75% ethyl acetate in hexanes). Concentration in vacuo of the product-rich fractions provided the titled compound as a pale-yellow solid (8 mg, 7%).
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