(Morpholin-3-yl)methanol hydrochloride → Ethyl 4-(2-bromo-4-fluorophenyl)-6-((3-(hydroxymethyl)morpholino)methyl)-2-(5-(trifluoromethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524827Notes

Reaction equation

HRID 524827 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][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][N:26]=2)=[N:10]1.Cl.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH:33]1[CH2:38][OH:39]>>[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:32]2[CH2:37][CH2:36][O:35][CH2:34][CH:33]2[CH2:38][OH:39])[NH:12][C:11]([C:22]2[S:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][N:26]=2)=[N:10]1

Participants

3

Reactant 2

HCID 22342713(Morpholin-3-yl)methanol hydrochlorideHCID 118107535Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(5-(trifluoro methyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 90043451Ethyl 4-(2-bromo-4-fluorophenyl)-6-((3-(hydroxymethyl)morpholino)methyl)-2-(5-(trifluoromethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 43.1%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(5-(trifluoromethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.74 g, 1.3 mmol) was reacted with morpholin-3-ylmethanol hydrochloride (0.23 g, 1.5 mmol) according to the procedure as described in Example 25, Step B to give the title compound as a yellowish solid (0.34 g, 43%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-f7866bbbb5994dd18f4d3d033bfc1eaf
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

Loading…