Morpholine-2-carboxylic acid → 4-((6-(2,4-Dichlorophenyl)-5-(ethoxycarbonyl)-2-(3-fluoropyridin-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxylic acid

HRID 524731Notes

Reaction equation

HRID 524731 reaction equation
Br[CH2:2][C:3]1[NH:8][C:7]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:6][CH:5]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[C:4]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].[NH:29]1[CH2:34][CH2:33][O:32][CH:31]([C:35]([OH:37])=[O:36])[CH2:30]1>>[Cl:23][C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[CH:5]1[N:6]=[C:7]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][N:10]=2)[NH:8][C:3]([CH2:2][N:29]2[CH2:34][CH2:33][O:32][CH:31]([C:35]([OH:37])=[O:36])[CH2:30]2)=[C:4]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

3

Reactant 2

HCID 21899747Morpholine-2-carboxylic acidHCID 118107608Ethyl 6-(bromomethyl)-4-(2,4-dichlorophenyl)-2-(3-fluoropyridin-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 732972124-((6-(2,4-Dichlorophenyl)-5-(ethoxycarbonyl)-2-(3-fluoropyridin-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxylic acidYield 43%

Procedure

Ethyl 6-(bromomethyl)-4-(2,4-dichlorophenyl)-2-(3-fluoropyridin-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.75 g, 1.53 mmol) was reacted with morpholine-2-carboxylic acid (0.26 g, 1.53 mmol) according to the procedure as described in Example 1, Step C to give the title compound as a yellow solid (0.35 g, 43%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-cebe95fc197f4d01b695dad4c757eec7
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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