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

HRID 524826Notes

Reaction equation

HRID 524826 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]([O:27][CH3:28])=[CH:25][N:26]=2)=[N:10]1.Cl.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH:31]1[CH2:36][OH:37]>>[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:30]2[CH2:35][CH2:34][O:33][CH2:32][CH:31]2[CH2:36][OH:37])[NH:12][C:11]([C:22]2[S:23][C:24]([O:27][CH3:28])=[CH:25][N:26]=2)=[N:10]1

Participants

3

Reactant 2

HCID 22342713(Morpholin-3-yl)methanol hydrochlorideHCID 90043009Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(5-methoxy thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 73295471Ethyl 4-(2-bromo-4-fluorophenyl)-6-((3-(hydroxymethyl)morpholino)methyl)-2-(5-methoxythiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 48%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(5-methoxythiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.53 g, 1 mmol) was reacted with morpholin-3-ylmethanol hydrochloride (0.18 g, 1.2 mmol) according to the procedure as described in Example 25, Step B to give the title compound as a yellowish solid (0.27 g, 48%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-705c3931ef63400ca8ef77647b5c55bf
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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