Dimethylformamide → HCID 12959657, compound

HRID 1287247Notes

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].CN(C)C=O.[H-].[Na+].C1(=O)O[CH2:32][CH2:31][O:30]1>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]([CH2:32][CH2:31][OH:30])[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 2.8 g of 1-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4 (1H,3H)-dione and 30 ml of dimethylformamide was added 0.53 g of 55 % sodium hydride, and the solution was heated up to 150°C. To this was added 0.97 g of ethylene carbonate, and the mixture was reacted for one hour at 150°C. After the reaction was complete, the solvent was distilled off from the resulting mixture under reduced pressure. To the residue obtained was added water to precipitate a crude product. This product was recrystallized from methanol to yield 2.8 g of 1-(m-nitrophenyl)-3-(2-hydroxyethyl)pyrido[2,3-d] pyrimidine-2,4(1H,3H)-dione as pale yellow prisms, melting at 212°-213°C.

Workup

customthe mixture was reacted for one hour at 150°C
distillationthe solvent was distilled off from the resulting mixture under reduced pressure
customTo the residue obtained
customto precipitate a crude product
customThis product was recrystallized from methanol

Sources & evidence

ORD record: ord-3174b789a5e1402ea53322581776f6a7
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03984415

Reaction notes

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