Water → HCID 71235044, compound

HRID 874505Notes

Reaction equation

HRID 874505 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][OH:6].[H-].[Na+].Cl[C:15]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:18]=[C:17]([S:26][CH3:27])[N:16]=1.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][O:6][C:19]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15][N:16]=[C:17]([S:26][CH3:27])[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 4312004(3-Chloro-4-methoxyphenyl)methanol

Product 1

HCID 71235044HCID 71235044, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chloro-4-methoxybenzyl alcohol (20 g, 116 mmol) was dissolved in 200 mL of DMF, NaH (7.0 g, 174 mmol) was added under ice-water-bath. After 1 h of reaction, ethyl 4-chloro-2-(methylmercapto)pyrimidine-5-carboxylate (27 g, 116 mmol) was added in portions for continuing the reaction for 3 h. 300 mL of water was added, extraction was performed with ethyl acetate, the organic layer was dried, concentrated and separated with silica gel column (petroleum ether: ethyl acetate=10:1) to obtain ethyl 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylate as white solid (5.0 g, 12%).

Workup

  1. additionwas added in portions
  2. customthe reaction for 3 h
  3. extractionextraction
  4. customthe organic layer was dried
  5. concentrationconcentrated
  6. customseparated with silica gel column (petroleum ether: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-1e22d2bec8424f4c83a99c39f708b763
Source dataset
uspto-grants-2015_03
Patent number
US08980904B2

Reaction notes

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