L-Proline → (2S)-1-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(1H-1,2,4-triazol-1-yl)-3,6-dihydropyrimidin-4-yl)methyl)pyrrolidine-2-carboxylic acid

HRID 524715Notes

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]([N:22]2[CH:26]=[N:25][CH:24]=[N:23]2)=[N:10]1.[NH:27]1[CH2:31][CH2:30][CH2:29][C@H:28]1[C:32]([OH:34])=[O:33]>>[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]([N:22]2[CH:26]=[N:25][CH:24]=[N:23]2)[NH:12][C:13]([CH2:20][N:27]2[CH2:31][CH2:30][CH2:29][C@H:28]2[C:32]([OH:34])=[O:33])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Reactant 2

HCID 145742L-Proline

HCID 90042258Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(1H-1,2,4-triazol-1-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107560(2S)-1-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(1H-1,2,4-triazol-1-yl)-3,6-dihydropyrimidin-4-yl)methyl)pyrrolidine-2-carboxylic acidYield 33.5%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(1H-1,2,4-triazol-1-yl)-1,4-dihydropyrimidine-5-carboxylate (0.5 g, 1.03 mmol) was reacted with (S)-pyrrolidine-2-carboxylic acid (0.12 g, 1.03 mmol) according to the procedure as described in Example 28 to give the title compound as a yellow solid (0.18 g, 33%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record: ord-dd34444c8d6b4a7e9d7eb34f8b3e49d5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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