Potassium Carbonate → 1-(3-Nitrophenyl)-3-[(pyridin-4-yl)methyl]pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 257787Notes

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].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>CC(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]([CH2:30][C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(3-Nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (12.0 g, 42.2 mmoles) was added into 2 liters of acetone and warmed with stirring until a solution was formed. To the solution was added powdered potassium carbonate (23.4 g, 169.3 mmoles) and 4-chloromethylpyridine hydrochloride (10.4 g, 63.4 mmoles). The solution was stirred at reflux temperature for 18 hours. The solution was filtered while hot. Three quarters of the solvent was removed resulting in the formation of a precipitate. The solution was cooled to 0° C. and the precipitate was removed by filtration. The precipitate was washed with ethyl ether and air dried yielding 10.0 g (26.6 mmole, 63% yield) of 1-(3-nitrophenyl)-3-(4-pyridylmethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (mp 207°-209° C.).

Workup

temperaturewarmed
customwas formed
stirringThe solution was stirred
temperatureat reflux temperature for 18 hours
filtrationThe solution was filtered while hot
customThree quarters of the solvent was removed
customresulting in the formation of a precipitate
customthe precipitate was removed by filtration
washThe precipitate was washed with ethyl ether and air
customdried

Sources & evidence

ORD record: ord-b1b9e512781043e2bfd7eec8c5be498f
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05264437

Reaction notes

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