Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate → Ethyl 4-(2-bromo-4-fluorophenyl)-6-((3-(isopropylcarbamoyl)morpholino)methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524691Notes

Reaction equation

HRID 524691 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.[CH:27]([NH:30][C:31]([CH:33]1[CH2:38][O:37][CH2:36][CH2:35][NH:34]1)=[O:32])([CH3:29])[CH3:28]>>[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][N:34]2[CH2:35][CH2:36][O:37][CH2:38][CH:33]2[C:31](=[O:32])[NH:30][CH:27]([CH3:28])[CH3:29])[NH:12][C:11]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[N:10]1

Participants

3

Reactant 2

HCID 59495567Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateHCID 65438161N-Isopropylmorpholine-3-carboxamide

Product 1

HCID 73295126Ethyl 4-(2-bromo-4-fluorophenyl)-6-((3-(isopropylcarbamoyl)morpholino)methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 35%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.6 g, 1.2 mmol) was reacted with N-isopropylmorpholine-3-carboxamide (0.21 g, 1.2 mmol) according to the procedure as described in Example 24 to give the title compound as a yellow solid (0.25 g, 35%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-cd4f4ce27612475f80f462b3c4caf4ae
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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