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

HRID 524760Notes

Reaction equation

HRID 524760 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.[N:28]1[CH:32]([CH:33]2[CH2:38][O:37][CH2:36][CH2:35][NH:34]2)[N:31]=[N:30][N:29]=1>>[N:31]1[CH:32]([CH:33]2[N:34]([CH2:20][C:13]3[NH:12][C:11]([C:22]4[S:23][CH:24]=[CH:25][N:26]=4)=[N:10][CH:9]([C:3]4[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[Br:1])[C:14]=3[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:35][CH2:36][O:37][CH2:38]2)[N:28]=[N:29][N:30]=1

Participants

3

Reactant 2

HCID 59495567Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateHCID 900434363-(5H-tetrazol-5-yl)morpholine hydrochloride

Product 1

HCID 90043838Ethyl 6-((3-(5H-tetrazol-5-yl)morpholino)methyl)-4-(2-bromo-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 42%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.5 g, 1 mmol) was reacted with 3-(5H-tetrazol-5-yl)morpholine hydrochloride (0.19 g, 1 mmol) according to the procedure as described in Example 28 to give the title compound as a yellow solid (0.24 g, 42%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-50f4c650d2e249d6822f82c3f0929f00
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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