Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:12]=[CH:11][O:10][C:9]=2[CH3:13])[CH:5]=[CH:4][N:3]=1.[CH3:14][C@H:15]1[O:20][C@@H:19]([CH3:21])[CH2:18][NH:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:21][C@H:19]1[O:20][C@@H:15]([CH3:14])[CH2:16][N:17]([C:2]2[N:7]=[C:6]([C:8]3[CH:12]=[CH:11][O:10][C:9]=3[CH3:13])[CH:5]=[CH:4][N:3]=2)[CH2:18]12-Chloro-4-(2-methyl-3-furanyl)pyrimidine (686 mg, 3.52 mmol), cis-2,6-dimethylmorpholine (447 mg, 3.88 mmol) and potassium carbonate (536 mg, 3.88 mmol) were added together in ethanol (16 mL) and the resulting mixture was heated under reflux for 4 hours. A further quantity of cis-2,6-dimethylmorpholine (122 mg, 1.057 mmol) and potassium carbonate (146 mg, 1.057 mmol) were added and the resulting mixture was heated under reflux for 4 hours. The reaction mixture was allowed to cool to room temperature and left to stand overnight. The reaction mixture was filtered, the filtrate evaporated under reduced pressure and the residue purified by SP4 Biotage column chromatography eluting with a gradient of 0-30% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound (737 mg, 2.70 mmol, 76% yield) as a colourless oil. LC/MS [M+H]+=274.
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