Ethanolamine → Ethyl 4-(2-bromo-4-fluorophenyl)-6-((2-((2-hydroxyethyl)carbamoyl)morpholino) methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524655Notes

Reaction equation

HRID 524655 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[N:14]=[C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[NH:12][C:11]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH:23]([C:27]([OH:29])=O)[CH2:22]2)=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].[NH2:35][CH2:36][CH2:37][OH:38]>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:10]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:11]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH:23]([C:27](=[O:29])[NH:35][CH2:36][CH2:37][OH:38])[CH2:22]2)[NH:12][C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[N:14]1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 732961284-((6-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxylic acid

Product 1

HCID 118107587Ethyl 4-(2-bromo-4-fluorophenyl)-6-((2-((2-hydroxyethyl)carbamoyl)morpholino) methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 60%

Procedure

4-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxylic acid (0.5 g, 0.9 mmol) was reacted with 2-aminoethanol (72 mg, 1.2 mmol) according to the procedure as described in Example 53 to give the title compound as a yellow solid (0.32 g, 60%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-544f5b6814274d40ac6da1aaeadb5c5f
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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