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

HRID 524640Notes

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][CH2:23][CH:22]2[C:27](=[O:35])[NH:28][CH2:29][C:30]([O:32]CC)=[O:31])[NH:12][C:11]([C:36]2[S:37][CH:38]=[CH:39][N:40]=2)=[N:10]1.[OH-].[Na+]>C(O)C.O>[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][CH2:23][CH:22]2[C:27]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:35])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of ethyl 4-(2-bromo-4-fluorophenyl)-6-((3-((2-ethoxy-2-oxoethyl)carbamoyl)morpholino)methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.2 g, 0.31 mmol) and sodium hydroxide (0.13 g, 3.1 mmol) in ethanol (6 mL) and water (1 mL) was stirred at 25° C. for 20 minutes. The reaction solution was adjusted to pH 6-7 with con. HCl, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=25/1) to give the title compound as a yellow solid (0.14 g, 74%). The compound was characterized by the following spectroscopic data:

Workup

concentrationHCl, and concentrated in vacuo
customThe residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=25/1)

Sources & evidence

ORD record: ord-5ee817a4b14e489d88c16db9eca601d1
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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