Triethylamine → Methyl 2-(4,6-dimethoxy-pyrimidin-2-ylthio)-3-methoxy-3,3-diphenylpropionate

HRID 251405Notes

Reaction equation

HRID 251405 reaction equation
O[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].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:34][O:35][C:36]1[CH:41]=[C:40]([O:42][CH3:43])[N:39]=[C:38]([SH:44])[N:37]=1.C(=O)(O)[O-].[Na+]>ClCCl.CN(C=O)C>[CH3:43][O:42][C:40]1[CH:41]=[C:36]([O:35][CH3:34])[N:37]=[C:38]([S:44][CH:2]([C:7]([O:20][CH3:21])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:3]([O:5][CH3:6])=[O:4])[N:39]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 10541193Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropanoateHCID 178493561HCID 178493561, compound

Product 1

HCID 12073751Methyl 2-(4,6-dimethoxy-pyrimidin-2-ylthio)-3-methoxy-3,3-diphenylpropionate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

7.16 g (25 mmol) of methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate were dissolved in 50 ml of dichloromethane, 3 g (30 mmol) of triethylamine were added, and 3.2 g (28 mmol) of methanesulfonyl chloride were added dropwise while stirring. The mixture was stirred at room temperature for 2 h, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was taken up in DMF and added dropwise at 0° C. to a suspension of 12.9 g (75 mmol) of 4,6-dimethoxypyrimidine-2-thiol and 8.4 g (100 mmol) of sodium bicarbonate in 100 ml of DMF. After stirring at room temperature for 2 h and at 60° C. for a further 2 h, the mixture was poured into 1 liter of ice-water, and the resulting precipitate was filtered off with suction. After drying, 3.19 g (29%) of a white powder remained.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. stirringAfter stirring at room temperature for 2 h and at 60° C. for a further 2 h
  6. filtrationthe resulting precipitate was filtered off with suction
  7. customAfter drying

Sources & evidence

ORD record
ord-3c04945f826340d9a6d6c4f4e1da46fe
Source dataset
uspto-grants-2011_01
Patent number
US07863445B2

Reaction notes

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