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

HRID 356867Notes

Reaction equation

HRID 356867 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.[Na].CN(C=O)C>ClCCl>[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

7

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15292268Methyl 3-benzyloxy-3-phenyl-2-hydroxybutyrateHCID 86746767Sodium dimethylformamideHCID 178493561HCID 178493561, compound

Product 1

HCID 15292275Methyl 3-benzyloxy-3-phenyl-2-(4,6-dimethoxypyrimidin-2-ylthio)-butyrateYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11 g (25 mmol) of methyl 3-benzyloxy-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 DMF and added dropwise to a suspension of 12.9 g (75 mmol) of 4,6-dimethoxypyrimidine-2-thiol and 8.4 g (100 nmol) of sodium 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 3.2 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-3cfcf8f88c6248a289a5131a0e00c216
Source dataset
uspto-grants-1998_11
Patent number
US05840722

Reaction notes

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