Potassium Carbonate → 6-(4-Methoxy-3-methylphenyl)pyrido[3,2-d]pyrimidin-4(1H)-one

HRID 1517414Notes

Reaction equation

HRID 1517414 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][NH:8][C:9](=[O:12])[C:10]=2[N:11]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][C:16]=1[CH3:24].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:24][C:16]1[CH:17]=[C:18]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]=[CH:7][NH:8][C:9](=[O:12])[C:10]=3[N:11]=2)[CH:19]=[CH:20][C:15]=1[O:14][CH3:13]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2773487(4-Methoxy-3-methylphenyl)boronic acidHCID 1354270966-Chloropyrido[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 1362700176-(4-Methoxy-3-methylphenyl)pyrido[3,2-d]pyrimidin-4(1H)-oneYield 77%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-chloro-pyrido[3,2-d]pyrimidin-4(3H)one (1.94 mmole) in 1,4-dioxane (40 ml) and water (20 ml) was added 4-methoxy-3-methylphenyl boronic acid (2.33 mmole), potassium carbonate (4.85 mmole) and tetrakis(triphenylphosphine)palladium(0) (0.097 mmole). The reaction mixture was refluxed for two hours, cooled to room temperature and the solvents were evaporated in vacuo. The residue was adsorbed on silica and purified by silica gel column chromatography (the mobile phase being a methanol/dichloromethane mixture in a ratio of 3:97), affording the title compound as a pure white powder (398 mg, yield 77%) which was characterized by its mass spectrum as follows: MS (m/z): 268 ([M+H]+, 100).

Workup

  1. temperatureThe reaction mixture was refluxed for two hours
  2. customthe solvents were evaporated in vacuo
  3. custompurified by silica gel column chromatography (the mobile phase

Sources & evidence

ORD record
ord-4d579396fa834afd8c9bd646996fbc62
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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