Phenol → 6-(4-Fluorophenyl)-4-phenoxypyrido[3,2-d]pyrimidine

HRID 1517441Notes

Reaction equation

HRID 1517441 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:11]1[C:12]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH:18]=[CH:17][C:13]=2[N:14]=[CH:15][N:16]=1>O1CCOCC1>[O:7]([C:11]1[C:12]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH:18]=[CH:17][C:13]=2[N:14]=[CH:15][N:16]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 579067564-Chloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidine

Product 1

HCID 576983476-(4-Fluorophenyl)-4-phenoxypyrido[3,2-d]pyrimidineYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of phenol (94 mg, 1 mmol) in dioxane (5 ml) was added sodium hydride (40 mg of a 60% dispersion in mineral oil, 1.0 mmol). The mixture was stirred at room temperature for 10 minutes. Then, 4-chloro-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine (52 mg, 0.2 mmol) was added to this solution. The resulting mixture was stirred at room temperature for another 30 minutes. After concentration under reduced pressure, the residue was purified by silica gel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane, in a volume ratio of 1:60, yielding the title compound (60 mg, yield 95%) as a white solid which was characterised by its mass spectrum as follows: MS (m/z): 318 ([M+H]+, 100).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for another 30 minutes
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue was purified by silica gel flash chromatography
  4. additiona mixture of methanol and dichloromethane

Sources & evidence

ORD record
ord-96bc3e0738444996a257257cf4e6ab72
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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