Sodium Hydroxide → 2-(2-(4-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-6-methyl-1,4-dihydropyrimidin-2-yl)thiazol-4-yl)acetic acid

HRID 524648Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[NH:12][C:11]([C:21]2[S:22][CH:23]=[C:24]([CH2:26][C:27]([O:29]C)=[O:28])[N:25]=2)=[N:10]1.[OH-].[Na+]>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[NH:12][C:11]([C:21]2[S:22][CH:23]=[C:24]([CH2:26][C:27]([OH:29])=[O:28])[N:25]=2)=[N:10]1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 90043962Ethyl 4-(2-bromo-4-fluorophenyl)-2-(4-(2-methoxy-2-oxoethyl)thiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 1181076312-(2-(4-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-6-methyl-1,4-dihydropyrimidin-2-yl)thiazol-4-yl)acetic acidYield 90.2%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-2-(4-(2-methoxy-2-oxoethyl)thiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate (1 g, 2 mmol) was reacted with sodium hydroxide (0.24 g, 6 mmol) according to the procedure as described Example 58, Step B to give the title compound as a yellow solid (0.87 g, 90%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record: ord-e7f3c40a009647298b9f55e2c8b9536f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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