Ethyl 3-(4-hydroxy-3-ethoxyphenyl)propionate → 3-{4-[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-3-ethoxy-phenyl}-propionic acid ethyl ester

HRID 1242391Notes

Reaction equation

HRID 1242391 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([O:14][CH2:15][CH3:16])[CH:8]=1)[CH3:2].Cl[CH2:19][C:20]1[C:21]([CH:36]2[CH2:38][CH2:37]2)=[N:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)=[N:24][CH:25]=1>>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:19][C:20]2[C:21]([CH:36]3[CH2:38][CH2:37]3)=[N:22][C:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:30][CH:31]=3)=[N:24][CH:25]=2)=[C:9]([O:14][CH2:15][CH3:16])[CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 21224444Ethyl 3-(4-hydroxy-3-ethoxyphenyl)propionateHCID 219359605-Chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine

Product 1

HCID 670724583-{4-[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-3-ethoxy-phenyl}-propionic acid ethyl ester

Procedure

In analogy to the procedures described in examples 8A] and 31B], 3-(3-ethoxy-4-hydroxy-phenyl)-propionic acid ethyl ester [Eur. Pat. Appl. (1996), EP 710659/A1] was reacted with 5-chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 27F]) to give 3-{4-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-3-ethoxy-phenyl}-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as colorless solid.

Sources & evidence

ORD record
ord-06d0d9e3ffab44e2a86c4d1430f4bbed
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…