Sodium Hydroxide → 2-(4-((6-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxamido)acetic acid

HRID 524657Notes

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]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH:23]([C:27](=[O:35])[NH:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH2:22]2)[NH:12][C:11]([C:36]2[S:37][CH:38]=[CH:39][N:40]=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[N:10]=[C:11]([C:36]2[S:37][CH:38]=[CH:39][N:40]=2)[NH:12][C:13]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH:23]([C:27]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:35])[CH2:22]2)=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 118107586Ethyl 4-(2-bromo-4-fluorophenyl)-6-((2-((2-ethoxy-2-oxoethyl)carbamoyl)morpholino)methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 900438422-(4-((6-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxamido)acetic acidYield 88%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-((2-((2-ethoxy-2-oxoethyl)carbamoyl)morpholino)methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.5 g, 0.8 mmol) was reacted with sodium hydroxide (0.32 g, 8 mmol) according to the procedure as described in Example 58, Step B to give the title compound as a yellow solid (0.43 g, 88%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record: ord-175248f8a6604e7cba94e684f8a742ee
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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