Benzyl Bromide → HCID 69733083, compound

HRID 2416423Notes

Reaction equation

HRID 2416423 reaction equation
[C:1]([O:4][C@H:5]([CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:17](=[O:22])[CH:18]=[C:19]([CH3:21])[NH:20][C:13]=2[N:12]([CH3:23])[C:11]1=[O:24])(=[O:3])[CH3:2].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([O:4][C@H:5]([CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:17](=[O:22])[CH:18]=[C:19]([CH3:21])[N:20]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:13]=2[N:12]([CH3:23])[C:11]1=[O:24])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 69733596HCID 69733596, compound

Product 1

HCID 69733083HCID 69733083, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (R)-3-(5-acetoxyhexyl)-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.84 g, 5.27 mmol), acetonitrile (20 ml), benzyl bromide (0.95 ml, 7.91 mmol) and potassium carbonate (2.19 g, 15.8 mmol) was stirred at 50° C. for 2 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was treated with water (50 ml) and extracted with ethyl acetate (50 ml). The organic extract was concentrated under reduced pressure to afford crude (R)-3-(5-acetoxyhexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe residue was treated with water (50 ml)
  4. extractionextracted with ethyl acetate (50 ml)
  5. extractionThe organic extract
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-dab71275069d4627b1a6a16ece283808
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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