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

HRID 524728Notes

Reaction equation

HRID 524728 reaction equation
Br[CH2:2][C:3]1[NH:8][C:7]([C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)=[N:6][CH:5]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[Cl:22])[C:4]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH:29]1[C:34]([OH:36])=[O:35]>>[Cl:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[CH:5]1[N:6]=[C:7]([C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)[NH:8][C:3]([CH2:2][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH:29]2[C:34]([OH:36])=[O:35])=[C:4]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

3

Reactant 2

HCID 33401523-Morpholinecarboxylic acidHCID 118107543Ethyl 6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(pyrazin-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 900434834-((6-(2-Chloro-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(pyrazin-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acidYield 29%

Procedure

Ethyl 6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(pyrazin-2-yl)-1,4-dihydropyrimidine-5-carboxylate (1 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 (0.32 g, 29%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-9f4dd4b818ff40cf9eea65e49140ded0
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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