Sodium hydride → [Rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethoxy}-2-methyl-phenoxy)-acetic acid ethyl ester

HRID 1242326Notes

Reaction equation

HRID 1242326 reaction equation
Cl[CH:2]([C:4]1[C:5]([CH:20]2[CH2:22][CH2:21]2)=[N:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:8][CH:9]=1)[CH3:3].[CH2:23]([O:25][C:26](=[O:37])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]=1[CH3:36])[CH3:24].[H-].[Na+]>CN(C=O)C>[CH2:23]([O:25][C:26](=[O:37])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:2]([C:4]2[C:5]([CH:20]3[CH2:22][CH2:21]3)=[N:6][C:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)=[N:8][CH:9]=2)[CH3:3])=[CH:31][C:30]=1[CH3:36])[CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21935642[Rac]-5-(1-chloro-ethyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidineHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetate

Product 1

HCID 67072201[Rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethoxy}-2-methyl-phenoxy)-acetic acid ethyl esterYield 56.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

180 mg (0.551 mmol) of [rac]-5-(1-chloro-ethyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 28H), 116 mg (0.551 mmol) of (4-hydroxy-2-methyl-phenoxy)-acetic acid ethyl ester (WO02092590) and 31 mg (0.71 mmol) sodium hydride (55% in oil) were stirred in 3 ml DMF over night. The reaction mixture was partitioned between ether and water. The crude product was purified by chromatography over silica gel with AcOEt/heptane 1:4 to give 157 mg of pure [rac]-(4-{1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethoxy}-2-methyl-phenoxy)-acetic acid ethyl ester.

Workup

  1. customThe reaction mixture was partitioned between ether and water
  2. customThe crude product was purified by chromatography over silica gel with AcOEt/heptane 1:4

Sources & evidence

ORD record
ord-550c2c922e084a9fb3d95ba8af2c334e
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…