Benzyl Bromide → HCID 13259352, compound

HRID 257791Notes

Reaction equation

HRID 257791 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[CH2:13][NH:12][C:11]2=[O:20])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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[CH2:13][N:12]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:11]2=[O:20])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 132593461-(3-Nitrophenyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

Product 1

HCID 13259352HCID 13259352, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(3-Nitrophenyl)pyrido[2,3-d]pyrimidine-2(1H,3H)-one (300 mg, 1.1 mmole) was suspended in acetone (100 ml). To this suspension was added powdered K2CO3 (607 mg, 4.4 mmole) and benzyl bromide (282 mg, 1.65 mmole). The suspension was refluxed for 18 hours. The suspension was filtered, while still hot, to remove solid unreacted K2CO3, which was discarded. The solvents were removed from the filtrate and the residue was purified by preparative thin-layer chromatography (eluted with ethyl acetate) yielding 104 mg (0.289 mmole, 26% yield) of 1-(3-nitrophenyl)-3-benzylpyrido[2,3-d]pyrimidine-2(1H,3H)-one (mp 144°-145° C.), as a yellow solid.

Workup

  1. temperatureThe suspension was refluxed for 18 hours
  2. filtrationThe suspension was filtered
  3. customwhile still hot, to remove solid unreacted K2CO3, which
  4. customThe solvents were removed from the filtrate
  5. customthe residue was purified by preparative thin-layer chromatography (eluted with ethyl acetate)

Sources & evidence

ORD record
ord-607eea79319f473284e245d96d5567f1
Source dataset
uspto-grants-1993_11
Patent number
US05264437

Reaction notes

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