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

HRID 1242506Notes

Reaction equation

HRID 1242506 reaction equation
C([O:3][C:4](=[O:38])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]2[C:18]([CH:34]3[CH2:36][CH2:35]3)=[N:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=3)=[N:21][CH:22]=2)=[CH:11][C:10]=1[CH3:37])([CH3:7])[CH3:6])C.[Li+].[OH-]>C1COCC1.CCO.CCOCC>[CH:34]1([C:18]2[C:17]([CH2:16][S:15][C:12]3[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:38])=[O:3])=[C:10]([CH3:37])[CH:11]=3)=[CH:22][N:21]=[C:20]([C:23]3[CH:24]=[CH:25][C:26]([O:29][C:30]([F:31])([F:33])[F:32])=[CH:27][CH:28]=3)[N:19]=2)[CH2:36][CH2:35]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 536278302-{4-[4-Cyclopropyl-2-(4-trifluoromethoxy-phenyl)-pyrimidin-5-ylmethylsulfanyl]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester

Product 1

HCID 219358802-{4-[4-Cyclopropyl-2-(4-trifluoromethoxy-phenyl)-pyrimidin-5-ylmethylsulfanyl]-2-methyl-phenoxy}-2-methyl-propionic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.386 g (0.7 mmol) of the above prepared 2-{4-[4-cyclopropyl-2-(4-trifluoromethoxy-phenyl)-pyrimidin-5-ylmethylsulfanyl]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester was dissolved in 12 ml of THF/EtOH (1:1), treated at 0° C. with 2.12 ml (2.1 mmol) of 1N LiOH, and kept at ambient temperature for 23 h. The reaction mixture was taken up in ether and washed with aqueous 10% KHSO4 solution and aqueous 10% NaCl solution. The water phases were extracted with ether (2×). The organic phase was dried (Na2SO4) and evaporated. The crude product was precipitated in ether/pentane (RT to 4° C.) and filtered to give 0.289 g of the title compound as white crystals of mp. 127–128° C., dec.

Workup

  1. washwashed with aqueous 10% KHSO4 solution and aqueous 10% NaCl solution
  2. extractionThe water phases were extracted with ether (2×)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe crude product was precipitated in ether/pentane (RT to 4° C.)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-3d711fa6c1e544738588524c729f51d9
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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