Benzyl Alcohol → Benzyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(6-methoxypyridin-2-yl)benzoate

HRID 865917Notes

Reaction equation

HRID 865917 reaction equation
C(O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.[H-].[Na+].C[C:12]1([CH3:31])[O:17][C:16](=[O:18])[C:15]2[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[N:24]=3)=[CH:20][CH:21]=[CH:22][C:14]=2[O:13]1.[CH3:32][O:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[N:37]=[C:36](S(C)(=O)=O)[N:35]=1.P(=O)(O)(O)O>CN(C)C=O>[CH3:32][O:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[N:37]=[C:36]([O:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[N:24]=3)[C:15]=2[C:16]([O:17][CH2:12][C:31]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)=[O:18])[N:35]=1

Participants

7

Reactant 5

HCID 244Benzyl AlcoholHCID 1004Phosphoric AcidHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 152794162,2-Dimethyl-5-(6-methoxypyridin-2-yl)-4H-(1,3)benzodioxin-4-one

Product 1

HCID 15279417Benzyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(6-methoxypyridin-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.36 g of benzyl alcohol dissolved in 50 ml of dimethylformamide are treated with 380 mg of sodium hydride (80% strength in liquid paraffin) and the mixture is subsequently stirred at room temperature for 1 h. 3.0 g of 2,2-dimethyl-5-(6-methoxypyridin-2-yl)-4H-(1,3)benzo-dioxin-4-one are added, the mixture is stirred at room temperature for 3 h and 2.65 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine are finally added. The mixture is stirred at room temperature for 2 h, at 80° C. for 1.5 h and at 115° C. for 3 h, poured into ice-water containing phosphoric acid and extracted with ethyl acetate, and the extract is washed with water, dried over sodium sulfate and concentrated in vacuo. The crude product is purified by chromatography on silica gel 60 using cyclohexane/toluene/ethyl acetate.

Workup

  1. stirringthe mixture is stirred at room temperature for 3 h
  2. stirringThe mixture is stirred at room temperature for 2 h, at 80° C. for 1.5 h and at 115° C. for 3 h
  3. extractionextracted with ethyl acetate
  4. washthe extract is washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by chromatography on silica gel 60 using cyclohexane/toluene/ethyl acetate

Sources & evidence

ORD record
ord-463439dbe928402ea448df447f587d9e
Source dataset
uspto-grants-1996_10
Patent number
US05569640

Reaction notes

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