Lithium Hydroxide → (4-{[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acid

HRID 1242317Notes

Reaction equation

HRID 1242317 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:14][C:15]2[C:16]([CH:31]3[CH2:33][CH2:32]3)=[N:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:19][CH:20]=2)[CH3:13])=[CH:8][C:7]=1[CH3:34].[Li+].[OH-]>C1COCC1.CCOCC>[CH:31]1([C:16]2[C:15]([CH2:14][N:12]([CH3:13])[C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:35])=[O:2])=[C:7]([CH3:34])[CH:8]=3)=[CH:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:23][CH:22]=3)[N:17]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67072224(4-{[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acid methyl ester

Product 1

HCID 11784703(4-{[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acidYield 28.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 351 mg (0.72 mmol) (4-{[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acid methyl ester and 1.45 ml 1N LiOH in 4 ml of THF was stirred for 3 h at RT. The reaction mixture was taken up in ether and washed with 1N HCl and water. The crude product was suspended in AcOEt/heptane 1:19 to give 95.64 mg of pure (4-{[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acid.

Workup

  1. washwashed with 1N HCl and water

Sources & evidence

ORD record
ord-41b8475283ac42cd971f0ed4761e6fe9
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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