[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[Cl:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14](Cl)[N:13]=1.[H-].[Na+].Cl>C1COCC1>[Cl:11][C:12]1[N:13]=[C:14]([O:1][CH2:2][C:3]2[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=2)[C:6]#[N:7])[CH:15]=[N:16][CH:17]=1To a solution of 3-hydroxymethyl-benzonitrile (2.0 g, 15.0 mmol) and 2,6-dichloro-pyrazine (2.24 g, 15.0 mmol) in THF (150 mL) was added 60% NaH in mineral oil (0.9 g, 22.5 mmol). After stirring at ambient temperature for 2 h, the reaction mixture was poured into 1N HCl (100 mL) and extracted with Ethyl Acetate (1×250 mL). The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated to dryness. The crude material was chromatographed over Silica Gel (40 g) eluting with hexanes (1000 mL) followed by ethyl acetate (500 mL) to obtain 3.53 g of the desired pure product (I-3a) as a white solid.
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