5-Chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine → 3-{4-[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-2-methyl-phenyl}-propionic acid ethyl ester

HRID 1242390Notes

Reaction equation

HRID 1242390 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:14])[CH3:2].Cl[CH2:17][C:18]1[C:19]([CH:34]2[CH2:36][CH2:35]2)=[N:20][C:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[N:22][CH:23]=1>>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:17][C:18]2[C:19]([CH:34]3[CH2:36][CH2:35]3)=[N:20][C:21]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=3)=[N:22][CH:23]=2)=[CH:9][C:8]=1[CH3:14])[CH3:2]

Participants

3

Reactant 2

HCID 219359605-Chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidineHCID 21986481Ethyl 3-(4-hydroxy-2-methylphenyl)propanoate

Product 1

HCID 670724473-{4-[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-2-methyl-phenyl}-propionic acid ethyl ester

Procedure

In analogy to the procedures described in examples 8A] and 31B], 3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester 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]-2-methyl-phenyl}-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as colorless solid.

Sources & evidence

ORD record
ord-7401585372984646b0266999149befdd
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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