Cl[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH2:23][C:24]#[N:25])[CH:19]=[C:20]([CH3:22])[CH:21]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:15][C:16]1[CH:17]=[C:18]([CH:23]([C:2]2[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=2)[C:24]#[N:25])[CH:19]=[C:20]([CH3:22])[CH:21]=1
To a stirred mixture of 4-chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (47.63 g, 0.22 M) and (3-bromo-5-methyl-phenyl)-acetonitrile (42 g, 0.2 M) in anhydrous DMF (220 mL) in an ice-water bath under an atmosphere of nitrogen, was added 60% sodium hydride (16 g, 0.4 M) in portions. After stirring for 1 hr, the mixture was stirred at room temperature for overnight. The mixture was neutralized with aqueous saturated ammonium chloride solution. The crude product was extracted with ether and purified by silica gel column chromatography (eluent, ether:hexanes (1:7)) to afford 68 g (87%) of a white solid. m.p. 123-124° C.; 1H NMR (200 MHz, CDCl3) δ 1.11 (3H, d, J=6.9 Hz), 1.15 (3H, D, J=6.9 Hz), 2.32 (3H, s), 2.97 (1H, m), 4.00 (3H, s), 4.01 (3H, s), 5.34 (1H, s), 7.14 (1H, s), 7.28 (1H, s), 7.31 (1H, s).
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