Methanol → 2-{4-[4-Cyclopropyl-2-(4-trifluoromethoxy-phenyl)-pyrimidin-5-ylmethylsulfanyl]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester

HRID 1242505Notes

Reaction equation

HRID 1242505 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH:20]2[CH2:22][CH2:21]2)=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[CH2:23]([O:25][C:26](=[O:42])[C:27]([O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]C(=O)C)=[CH:33][C:32]=1[CH3:41])([CH3:29])[CH3:28])[CH3:24].CO.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH2:23]([O:25][C:26](=[O:42])[C:27]([O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37][CH2:2][C:3]2[C:4]([CH:20]3[CH2:22][CH2:21]3)=[N:5][C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)=[N:7][CH:8]=2)=[CH:33][C:32]=1[CH3:41])([CH3:28])[CH3:29])[CH3:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 219356455-Chloromethyl-4-cyclopropyl-2-(4-trifluoromethoxy-phenyl)-pyrimidineHCID 865978202-(4-Acetylsulfanyl-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester

Product 1

HCID 536278302-{4-[4-Cyclopropyl-2-(4-trifluoromethoxy-phenyl)-pyrimidin-5-ylmethylsulfanyl]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl esterYield 78.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.399 g (1.2 mmol) of 5-Chloromethyl-4-cyclopropyl-2-(4-trifluoromethoxy-phenyl)-pyrimidine (example 150D]) and 0.300 g (1.0 mmol) of 2-(4-acetylsulfanyl-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (example 142C]) were dissolved in 2.0 ml of acetonitrile and 0.08 ml of MeOH and treated with 0.462 g (1.4 mmol) of Cs2CO3. After vigorous stirring for 27 h at ambient temperature and filtration, the solvent was evaporated and the residue redissolved in dichloromethane and filtered again and evaporated. Purification by flash chromatography (SiO2, dichloromethane/n-heptane 1:2 to 4:1 and then AcOEt) afforded 0.428 g of the title compound as colorless oil.

Workup

  1. filtrationfiltration
  2. customthe solvent was evaporated
  3. dissolutionthe residue redissolved in dichloromethane
  4. filtrationfiltered again
  5. customevaporated
  6. customPurification by flash chromatography (SiO2, dichloromethane/n-heptane 1:2 to 4:1

Sources & evidence

ORD record
ord-95f1030987f24dc0897344210ed090ba
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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