[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[O:9]=[C:10]1[NH:15][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH2:23][CH:24]=[CH2:25])=[N:13][CH:12]=[C:11]1[C:26]#[N:27].Cl>O.O1CCCC1>[CH2:23]([O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]1[NH:15][C:10](=[O:9])[C:11]([C:26]2[NH:27][N:7]=[N:6][N:5]=2)=[CH:12][N:13]=1)[CH:24]=[CH2:25]Aluminum chloride (1.71 g., 0.0128 mole) followed by sodium azide (2.5 g., 0.0384 mole) was cautiously added to ice-cold, stirred tetrahydrofuran (100 ml.). The mixture was heated under reflux for 0.5 hour. To the mixture was added 1,6-dihydro-6-oxo-2-(2-allyloxyphenyl)pyrimidine-5-carbonitrile (3.23 g., 0.0128 mole) and refluxing was continued for 18 hours. The cooled reaction mixture was diluted with water and acidified with 6N hydrochloric acid. The precipitate was collected and recrystallized from 95% ethanol to give the title compound (1.4 g., 37%), m.p. 221°-225°. Two recrystallizations from acetic acid gave analytical material, m.p. 230.5°-232° (decomp).
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