[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]([OH:10])=O)[N:5]=[CH:4]1)[CH3:2].S(Cl)(Cl)=O.N1C=CC=CC=1.[CH2:21]([C:23]1[C:28]([NH2:29])=[CH:27][N:26]=[CH:25][N:24]=1)[CH3:22]>C1COCC1>[CH2:21]([C:23]1[C:28]([NH:29][C:8]([C:6]2[N:5]=[CH:4][N:3]([CH2:1][CH3:2])[CH:7]=2)=[O:10])=[CH:27][N:26]=[CH:25][N:24]=1)[CH3:22]A solution of 1-ethyl-1H-imidazole-4-carboxylic acid (2.5 g, 17.8 mmol) and thionyl chloride (65 mL) is refluxed for 1.5 h. The thionyl chloride is removed in vacuo using toluene to azeotrope thionyl chloride. To a suspension of the residue is added THF (60 mL) and pyridine (3.2 mL, 39.2 mmol), followed by 4-ethyl-5-pyrimidineamine (2.2 g, 17.8 mmol). The reaction mixture is refluxed for 17 h, and concentrated in vacuo. The residue is taken up in water (100 mL), and the pH of the solution is adjusted to 8.0 by the addition of solid potassium carbonate. The aqueous layer is extracted with methylene chloride (3×100 mL). The organic extracts are combined, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (300 g) using 3% MeOH in CH2Cl2 as eluent. The product fractions are combined and the solvent removed. The resultant material is triturated with ether+MeOH (19+1) to give the title compound.
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