Water → 3-benzyl-6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one

HRID 1749095Notes

Reaction equation

HRID 1749095 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7](=[O:12])[NH:8][CH2:9][C:10]=2[N:11]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C>[CH2:21]([N:8]1[CH2:9][C:10]2[N:11]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]1=[O:12])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 709815066-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one

Product 1

HCID 709805483-benzyl-6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-oneYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one (120 mg, 0.5 mmol, 1.0 equiv) in DMF (3 mL) was added sodium hydride (60% in mineral oil, 24 mg, 0.6 mmol, 1.2 equiv) and the reaction mixture was stirred for 1 h. Benzyl bromide (70 μL, 0.6 mmol, 1.2 equiv) was added and the mixture was stirred for 16 h. H2O was added and the product was extracted with EtOAc. The organic phase was washed with, brine, dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-40%) to afford 3-benzyl-6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one (112 mg). MS: [M+H]+=334.

Workup

  1. stirringthe mixture was stirred for 16 h
  2. extractionthe product was extracted with EtOAc
  3. washThe organic phase was washed with, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-40%)

Sources & evidence

ORD record
ord-5e48c906bbbc48ba990ebca7674799b7
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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