Benzyl Bromide → 1-(m-nitrophenyl)-3-benzylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[NH:12][C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[N:12]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]Participants
Procedure
To a mixture of 2.8 g of 1-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4 (1H,3H)-dione and 30 ml of dry dimethylformamide was added 0.6 g of approximately 50 % sodium hydride. The mixture was stirred for 30 minutes at room temperature and for additional 10 minutes at a temperature of 70°-80°C. To the mixture was further added dropwise 3.4 g of benzyl bromide and stirring was continued for 30 minutes. The solvent was removed from the resulting mixture by distillation, and to the residue was added water to give a crude precipitate. This product was recrystallized from a mixture of methanol and dimethylformamide to yield 3.3 g of 1-(m-nitrophenyl)-3-benzylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione as pale yellow prisms, melting at 219°-220°C.
Workup
- stirringstirring
- waitwas continued for 30 minutes
- customThe solvent was removed from the resulting mixture by distillation
- additionto the residue was added water
- customto give a crude precipitate
- customThis product was recrystallized from a mixture of methanol and dimethylformamide
Sources & evidence
- ORD record
- ord-7097bb5f1ca24ada96a0f2ac66b76599
- Source dataset
- uspto-grants-1976_10
- Patent number
- US03984415
Reaction notes
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