proline dl-form → HCID 73296577, compound

HRID 524713Notes

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[S:23][CH:24]=[CH:25][N:26]=2)=[N:10]1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH: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]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[NH:12][C:13]([CH2:20][N:27]2[CH2:31][CH2:30][CH2:29][CH: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 614proline dl-form

HCID 59495567Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 73296577HCID 73296577, compoundYield 25.1%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (1 g, 2 mmol) was reacted with pyrrolidine-2-carboxylic acid (0.23 g, 2 mmol) according to the procedure as described in Example 28 to give the title compound as a yellow solid (0.27 g, 25%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record: ord-433b0c3af7dc437aa5cc2af5c17ec23b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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