Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate → 2-Methyl-2-{2-methyl-4-[4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-phenoxy}-propionic acid ethyl ester

HRID 1242439Notes

Reaction equation

HRID 1242439 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:7])[CH3:6])[CH3:2].Cl[CH2:19][C:20]1[C:21]([C:36]([F:39])([F:38])[F:37])=[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])[C:5]([CH3:6])([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:19][C:20]2[C:21]([C:36]([F:39])([F:37])[F:38])=[N:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:28][CH:27]=3)=[N:24][CH:25]=2)=[CH:11][C:10]=1[CH3:16])[CH3:7])[CH3:2]

Participants

3

Reactant 2

HCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 219357875-Chloromethyl-4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine

Product 1

HCID 865978082-Methyl-2-{2-methyl-4-[4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-phenoxy}-propionic acid ethyl ester

Procedure

In analogy to the procedures described in example 101A], 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) was reacted with 5-chloromethyl-4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 107D]) to give 2-methyl-2-{2-methyl-4-[4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-phenoxy}-propionic acid ethyl ester, which was subsequently saponified in analogy to the procedure described in example 101B] to yield the title compound as off-white powder of mp. 149–151° C., dec.

Sources & evidence

ORD record
ord-e33035bdeaa544828e156a68155b4822
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…