Lithium Hydroxide → 2-(4-((2-Cyclopentyl-6-(trifluoromethyl)pyrimidin-4-yl)methyl)phenyl)acetic acid

HRID 1508941Notes

Reaction equation

HRID 1508941 reaction equation
[CH:1]1([C:6]2[N:11]=[C:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]C)=[O:21])=[CH:15][CH:14]=3)[CH:9]=[C:8]([C:24]([F:27])([F:26])[F:25])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+]>>[CH:1]1([C:6]2[N:11]=[C:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=3)[CH:9]=[C:8]([C:24]([F:26])([F:27])[F:25])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 90112127Methyl 2-(4-((2-cyclopentyl-6-(trifluoromethyl)pyrimidin-4-yl)methyl)phenyl)acetate

Product 1

HCID 742207132-(4-((2-Cyclopentyl-6-(trifluoromethyl)pyrimidin-4-yl)methyl)phenyl)acetic acidYield 25.4%

Procedure

Following general procedure D, methyl 2-(4-((2-cyclopentyl-6-(trifluoromethyl)pyrimidin-4-yl)methyl)phenyl)acetate (0.55 mmol) was reacted with lithium hydroxide (0.055 g) to afford the title compound (0.051 g, 25% over two steps) as a light yellow oil. MW=364.36. 1H NMR (DMSO-d6, 500 MHz) δ 12.27 (s, 1H), 7.72 (s, 1H), 7.28 (d, J=8.0 Hz, 2H), 7.20 (d, J=8.0 Hz, 2H), 4.17 (s, 2H), 3.52 (s, 2H), 3.41-3.33 (m, 1H), 2.08-1.99 (m, 2H), 1.89-1.60 (m, 6H); APCI MS m/z 365 [M+H]+.

Sources & evidence

ORD record
ord-628c077c0a7140ecbb1e02ae45a50a30
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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