Triethylamine → Methyl 3-benzyloxy-3-phenyl-2-(4,6-dimethoxypyrimidin-2-ylthio)-butyrate

HRID 1941108Notes

Reaction equation

HRID 1941108 reaction equation
[CH2:1]([O:8][C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH:10](O)[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:35][O:36][C:37]1[CH:42]=[C:41]([O:43][CH3:44])[N:40]=[C:39]([SH:45])[N:38]=1.C(=O)(O)[O-].[Na+]>ClCCl.CN(C)C=O>[CH2:1]([O:8][C:9]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH3:16])[CH:10]([S:45][C:39]1[N:38]=[C:37]([O:36][CH3:35])[CH:42]=[C:41]([O:43][CH3:44])[N:40]=1)[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 15292268Methyl 3-benzyloxy-3-phenyl-2-hydroxybutyrate2×HCID 178493561HCID 178493561, compound

Product 1

HCID 15292275Methyl 3-benzyloxy-3-phenyl-2-(4,6-dimethoxypyrimidin-2-ylthio)-butyrate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

11 g (25 mmol) of methyl 3-benzyloxy-3-phenyl-2-hydroxybutyrate (compound 1.1) are dissolved in 50 ml of dichloromethane, 3 g (30 mmol) of triethylamine are added and 3.2 g (28 mmol) of methanesulfonyl chloride are added dropwise while stirring. Stirring is continued for 2 hours at room temperature, and the mixture is washed with water, dried over magnesium sulfate and evaporated down under reduced pressure. The residue is taken up in dimethylformamide and the solution is 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 dimethylformamide. After stirring has been carried out for 2 hours at room temperature and for a further 2 hours at 60° C., the mixture is poured onto 11 of ice water and the resulting precipitate is filtered off with suction. After drying, 3.2 g of a white powder remain.

Workup

  1. stirringStirring
  2. washthe mixture is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down under reduced pressure
  5. stirringAfter stirring
  6. waithas been carried out for 2 hours at room temperature and for a further 2 hours at 60° C.
  7. filtrationthe resulting precipitate is filtered off with suction
  8. customAfter drying

Sources & evidence

ORD record
ord-8a492a0814644f0d9413dc4986875c9e
Source dataset
uspto-grants-1997_12
Patent number
US05703017

Reaction notes

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