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

HRID 1957092Notes

Reaction equation

HRID 1957092 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]2[CH:18]=[CH:19][CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[N:23]=3)[C:15]=2[C:14](=[O:30])[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:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[N:23]=3)[C:15]=2[C:14]([O:13][CH2:12][C:31]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)=[O:30])[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 about 1 h. 3.0 g of 2,2-dimethyl-5-(6-methoxypyridin-2-yl)-4H-(1,3)benzodioxin-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 organic phase is washed with water, dried over sodium sulfate and concentrated under reduced pressure. The crude product is purified by chromatography on silica gel 60 using cyclohexane/toluene/ethyl acetate. 1H-NMR (CDCl3): see Table 1.

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 organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by chromatography on silica gel 60 using cyclohexane/toluene/ethyl acetate

Sources & evidence

ORD record
ord-b2fcf38660c241979648aae25f45e55c
Source dataset
uspto-grants-1998_07
Patent number
US05783521

Reaction notes

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