Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate → HCID 73295975, compound

HRID 524630Notes

Reaction equation

HRID 524630 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.Cl.[C:28]([O:31][CH2:32][CH2:33][NH:34][C:35]([C@@H:37]1[CH2:42][O:41][CH2:40][CH2:39][NH:38]1)=[O:36])(=[O:30])[CH3:29]>>[C:28]([O:31][CH2:32][CH2:33][NH:34][C:35]([C@H:37]1[N:38]([CH2:20][C:13]2[NH:12][C:11]([C:22]3[S:23][CH:24]=[CH:25][N:26]=3)=[N:10][CH:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[Br:1])[C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:39][CH2:40][O:41][CH2:42]1)=[O:36])(=[O:30])[CH3:29]

Participants

3

Reactant 2

HCID 59495567Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateHCID 118107616HCID 118107616, compound

Product 1

HCID 73295975HCID 73295975, compoundYield 26.1%

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 (S)-2-(morpholine-3-carboxamido)ethyl acetate hydrochloride (0.3 g, 1.2 mmol) according to the procedure as described in Example 24 to give the title compound as a yellow solid (0.2 g, 26%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-c63286205d314a4aa81dab90f7d31b64
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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