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Potassium Carbonate → Methyl 3-[2-Methoxycarbonyl-2-(4-methoxy-6-methyl-2-pyrimidinyloxy)-1,1-diphenylethoxy]-2,2-dimethylpropionate

HRID 397332
Notes
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Reaction equation

HRID 397332 reaction equation
[OH:1][CH:2]([C:25]([O:27][CH3:28])=[O:26])[C:3]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7]([O:9][CH3:10])=[O:8].C([O-])([O-])=O.[K+].[K+].CS([C:39]1[N:44]=[C:43]([O:45][CH3:46])[CH:42]=[C:41]([CH3:47])[N:40]=1)(=O)=O>CN(C=O)C.O>[CH3:28][O:27][C:25]([CH:2]([O:1][C:39]1[N:44]=[C:43]([O:45][CH3:46])[CH:42]=[C:41]([CH3:47])[N:40]=1)[C:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[O:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7]([O:9][CH3:10])=[O:8])=[O:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27723804-Methoxy-6-methyl-2-(methylsulfonyl)pyrimidineHCID 15379668Methyl 3-(2-Hydroxy-2-methoxycarbonyl-1,1-diphenylethoxy)-2,2-dimethylpropionate

Product 1

HCID 15379669Methyl 3-[2-Methoxycarbonyl-2-(4-methoxy-6-methyl-2-pyrimidinyloxy)-1,1-diphenylethoxy]-2,2-dimethylpropionateYield 90%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

10 g (25.9 mmol) of methyl 3-(2-hydroxy-2-methoxycarbonyl-1,1-di-phenylethoxy)-2,2-dimethylpropionate were dissolved in 40 ml of DMF under N2, 1.78 g (13 mmol) of K2CO3 and 5.2 g (25.9 mmol) of 2-methanesulfonyl-4-methoxy-6-methylpyrimidine were added, and the mixture was stirred at 80° C. for 2 h. It was subsequently diluted with 40 ml of H2O and extracted twice with 30 ml of diethyl ether, the organic phase was dried over MgSO4 and concentrated, and the residue was purified by chromatography on silica gel with ethyl acetate/cyclohexane mixtures. Crystallization from diethyl ether/hexane resulted in 11.8 g (90%) of the product as colorless crystals.

Workup

  1. extractionextracted twice with 30 ml of diethyl ether
  2. dry with materialthe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography on silica gel with ethyl acetate/cyclohexane mixtures
  5. customCrystallization from diethyl ether/hexane

Sources & evidence

ORD record
ord-9981eb5c2fc342809771c1297032b1d5
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06610691B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes