Potassium Carbonate → 7-bromo-3-(2-methoxyethyl)pyrido[3,2-d]pyrimidin-4(3H)-one

HRID 1619373Notes

Reaction equation

HRID 1619373 reaction equation
[Br:1][C:2]1[CH:11]=[N:10][C:9]2[C:8](=[O:12])[NH:7][CH:6]=[N:5][C:4]=2[CH:3]=1.Br[CH2:14][CH2:15][O:16][CH3:17].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CN(C=O)C.O>[Br:1][C:2]1[CH:11]=[N:10][C:9]2[C:8](=[O:12])[N:7]([CH2:14][CH2:15][O:16][CH3:17])[CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 1356820527-bromo-3H,4H-pyrido(3,2-d)pyrimidin-4-one

Product 1

HCID 585743837-bromo-3-(2-methoxyethyl)pyrido[3,2-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-bromopyrido[3,2-d]pyrimidin-4(3H)-one (200 mg, 0.89 mmol), 1-bromo-2-methoxyethane (148 mg, 1.06 mmol) and K2CO3 (184 mg, 1.3 mmol) in acetone (10 mL) and DMF (3 mL) was stirred at room temperature for 4 h. Then the mixture was diluted with H2O (50 mL) and extracted with ethyl acetate (3×50 mL), the combined organic layers were washed with brine, dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product. MS (ESI): 284, 286 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5556129192144d94a976a8a41126fefc
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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