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

HRID 356870Notes

Reaction equation

HRID 356870 reaction equation
[O:1]([C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[CH:9](O)[C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.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>[O:1]([C:8]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:15])[CH:9]([S:44][C:38]1[N:37]=[C:36]([O:35][CH3:34])[CH:41]=[C:40]([O:42][CH3:43])[N:39]=1)[C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 15766824Methyl 3-phenoxy-3-phenyl-2-hydroxybutyrateHCID 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 (comp. 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 ml of DMF and added dropwise to a suspension of 12.9 g (75 mmol) of 4,6-dimethoxypyrimidine-2-thiol and 8.4 g (100 nm mmol) of sodium bicarbonate in 100 ml of DMF at 0° C. After stirring at room temperature for 2 hours and at 60° C. for a further 2 hours, the mixture is poured into 1 1 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 a further 2 hours
  6. filtrationthe precipitate is filtered off with suction
  7. customDrying

Sources & evidence

ORD record
ord-e9a4e9c8310345dfb92fa2f86c539160
Source dataset
uspto-grants-1998_11
Patent number
US05840722

Reaction notes

Loading…