3-Morpholinecarboxylic acid → 4-((6-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(2,4,6-trifluorophenyl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acid

HRID 524730Notes

Reaction equation

HRID 524730 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]Br)[NH:12][C:11]([C:22]2[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=2[F:30])=[N:10]1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH:32]1[C:37]([OH:39])=[O:38]>>[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:22]2[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=2[F:30])[NH:12][C:13]([CH2:20][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH:32]2[C:37]([OH:39])=[O:38])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 33401523-Morpholinecarboxylic acidHCID 118107540Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(2,4,6-tri fluorophenyl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 900429604-((6-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(2,4,6-trifluorophenyl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acidYield 33.3%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(2,4,6-trifluorophenyl)-1,4-dihydropyrimidine-5-carboxylate (1.21 g, 2.2 mmol) was reacted with morpholine-3-carboxylic acid (0.29 g, 2.2 mmol) according to the procedure as described in Example 1, Step C to give the title compound as a yellow solid (0.44 g, 33%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-0699d33d3f2147d588e7ad69d20cee73
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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