[CH3:1][C:2]1[CH:7]=[C:6](O)[CH:5]=[C:4]([CH3:9])[N:3]=1.[H-].[Na+].[Cl:12][C:13]1[CH:18]=[C:17](Cl)[N:16]=[CH:15][N:14]=1.Cl.C[N:22](C=O)C>>[Cl:12][C:13]1[N:14]=[CH:15][N:16]=[C:17]([NH:22][C:6]2[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([CH3:9])[CH:5]=2)[CH:18]=10.12 g (0.97 mmol) 2,6-dimethyl-4-hydroxypyridine and 55 mg (1.26 mmol) sodium hydride (60% dispersion in mineral oil) were dissolved in 1.5 mL DMF and stirred for 15 min. 0.15 g (0.98 mmol) 4,6-dichloropyrimidine were added and the mixture was stirred overnight at RT. The reaction mixture was acidified with a 4M hydrochloric acid, filtered and purified by preparative HPLC-MS. The fractions containing product were combined and freeze-dried.
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