Morpholine-2-carboxylic acid hydrochloride → 4-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(1-methyl-1H-1,2,4-triazol-3-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxylic acid

HRID 524695Notes

Reaction equation

HRID 524695 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[N:26]=[CH:25][N:24]([CH3:27])[N:23]=2)=[N:10]1.Cl.[NH:29]1[CH2:34][CH2:33][O:32][CH:31]([C:35]([OH:37])=[O:36])[CH2:30]1>>[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[N:26]=[CH:25][N:24]([CH3:27])[N:23]=2)[NH:12][C:13]([CH2:20][N:29]2[CH2:34][CH2:33][O:32][CH:31]([C:35]([OH:37])=[O:36])[CH2:30]2)=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 42614320Morpholine-2-carboxylic acid hydrochlorideHCID 90043165Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(1-methyl-1H-1,2,4-triazol-3-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 900436814-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(1-methyl-1H-1,2,4-triazol-3-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxylic acidYield 38.1%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(1-methyl-1H-1,2,4-triazol-3-yl)-1,4-dihydropyrimidine-5-carboxylate (1 g, 2 mmol) was reacted with morpholine-2-carboxylic acid hydrochloride (0.34 g, 2 mmol) according to the procedure as described in Example 1, Step C to give the title compound as a yellow solid (0.42 g, 38%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-49d39534de3a4980aae9caa1db4c9988
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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