Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → 3-[3,5-Difluoro-4-(4-isopropylsulfanyl-2-methyl-pyrimidin-5-yl methoxy)-phenyl]-propionic acid ethyl ester

HRID 62950Notes

Reaction equation

HRID 62950 reaction equation
[CH:1]([S:4][C:5]1[C:10]([CH2:11][OH:12])=[CH:9][N:8]=[C:7]([CH3:13])[N:6]=1)([CH3:3])[CH3:2].[CH2:14]([O:16][C:17](=[O:29])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23](O)=[C:22]([F:28])[CH:21]=1)[CH3:15]>>[CH2:14]([O:16][C:17](=[O:29])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([O:12][CH2:11][C:10]2[C:5]([S:4][CH:1]([CH3:3])[CH3:2])=[N:6][C:7]([CH3:13])=[N:8][CH:9]=2)=[C:22]([F:28])[CH:21]=1)[CH3:15]

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90118129(4-Isopropylsulfanyl-2-methyl-pyrimidin-5-yl)-methanol

Product 1

HCID 901181383-[3,5-Difluoro-4-(4-isopropylsulfanyl-2-methyl-pyrimidin-5-yl methoxy)-phenyl]-propionic acid ethyl esterYield 73.1%

Procedure

(4-Isopropylsulfanyl-2-methyl-pyrimidin-5-yl)-methanol (0.006 g, 0.03 mmol) obtained in Step B of Preparation Example 40 and 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (0.007 g, 0.03 mmol) obtained in Step D of Preparation Example 2 were reacted in the same manner as in Step A of Example 24 to obtain the title compound (0.009 g, 72%).

Workup

  1. customwere reacted in the same manner as in Step A of Example 24

Sources & evidence

ORD record
ord-df36060e43ff4839acff5cdb042b051c
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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