Water → Methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy3,3-diphenylpropionate

HRID 1801618Notes

Reaction equation

HRID 1801618 reaction equation
[OH:1][CH:2]([C:7]([O:20][CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[N:29]=[C:28](S(C)(=O)=O)[N:27]=1.O>CN(C)C=O.C(O)(=O)C>[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[N:29]=[C:28]([O:1][CH:2]([C:7]([O:20][CH3:21])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([O:5][CH3:6])=[O:4])[N:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 10541193Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropanoate

Product 1

HCID 10717204Methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy3,3-diphenylpropionate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

2.86 g (10 mmol) of methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate were dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride was added. The mixture was stirred for 1 h and then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added. After stirring at room temperature for 24 h, cautious hydrolysis was carried out with 10 ml of water, the pH was adjusted to 5 with acetic acid, and the solvent was removed by distillation under high vacuum. The residue was taken up in 100 ml of ethyl acetate, washed with water and dried over magnesium sulfate, and the solvent was distilled out. The residue was mixed with 10 ml of ether, and the resulting precipitate was filtered off with suction. After drying, 3.48 g (82%) of a white powder remained.

Workup

  1. stirringAfter stirring at room temperature for 24 h
  2. customcautious hydrolysis
  3. customthe solvent was removed by distillation under high vacuum
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled out
  7. additionThe residue was mixed with 10 ml of ether
  8. filtrationthe resulting precipitate was filtered off with suction
  9. customAfter drying

Sources & evidence

ORD record
ord-4e825118085d478aa46e604b6f1f36a2
Source dataset
uspto-grants-2013_01
Patent number
US08349843B2

Reaction notes

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