Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[OH:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15].[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[Cl:8][C:4]1[N:3]=[C:2]([O:9][CH2:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])[CH:7]=[N:6][CH:5]=1A mixture of 2,6-dichloropyrazine (400 mg, 0.671 mmol), 3-hydroxymethyl-benzonitrile (428 mg, 0.805 mmol), KOH (181 mg, 0.805 mmol) and 18-crown-6 (28 mg, 0.027 mmol) in toluene (10 mL) was stirred at reflux for 6 h and concentrated in vacuo. The residue was partitioned between H2O and ethyl acetate. The aqueous phase was separated and extracted with ethyl acetate twice. The combined organic extracts were washed with water and brine, dried and concentrated in vacuo. The crude product I-3f (667.2 mg) was used for next step without further purification.
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