Triethylamine → Methyl 3-phenoxy-3-phenyl-2-[(4,6-dimethoxy-2-pyrimidinyl)thio]butyrate

HRID 378365Notes

Reaction equation

HRID 378365 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]C=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=O)C>[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:1]1[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=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 15292300Methyl 3-phenoxy-3-phenyl-2-[(4,6-dimethoxy-2-pyrimidinyl)thio]butyrateYield 38.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

7.2 g (25 mmol) of methyl 3-phenoxy-3-phenyl-2-hydroxybutyrate (Compound 1.1) are dissolved in 50 ml of dichloromethane, 3 g (30 mmol) of triethylamine are added and, while stirring, 3.2 g (28 mmol) of methanesulfonyl chloride are added dropwise. The mixture is stirred at room temperature for 2 hours, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is taken up in 100 mo of DMF and added dropwise to a suspension 12.9 g (75 mmol) of 4,6-dimethoxypyrimidine-2-thiol and 8.4 g (100 mmol) sodium bicarbonate in 100 ml of DMF at 0° C. After stirring at room temperature for 2 hours and at 60° C. for further 2 hours, the mixture is poured into 1 liter of ice-water, and the precipitate is filtered off with suction. Drying results in 4.2 g of a white powder.

Workup

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

Sources & evidence

ORD record
ord-51f43ff620c64095b90bfe1cffaab82a
Source dataset
uspto-grants-2000_02
Patent number
US06030975

Reaction notes

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