6-Bromomethyl-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester → (3S)-4-((6-(2-chloro-4-fluorophenyl)-5-(methoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)-2,2-dimethylmorpholine-3-carboxylic acid

HRID 524619Notes

Reaction equation

HRID 524619 reaction equation
Br[CH2:2][C:3]1[NH:8][C:7]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[N:6][CH:5]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[Cl:21])[C:4]=1[C:22]([O:24][CH3:25])=[O:23].[CH3:26][C:27]1([CH3:36])[O:32][CH2:31][CH2:30][NH:29][C@@H:28]1[C:33]([OH:35])=[O:34]>>[Cl:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[CH:5]1[N:6]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[NH:8][C:3]([CH2:2][N:29]2[CH2:30][CH2:31][O:32][C:27]([CH3:26])([CH3:36])[C@H:28]2[C:33]([OH:35])=[O:34])=[C:4]1[C:22]([O:24][CH3:25])=[O:23]

Participants

3

Reactant 2

HCID 899959636-Bromomethyl-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl esterHCID 90043546(S)-2,2-dimethylmorpholine-3-carboxylic acid

Product 1

HCID 118107558(3S)-4-((6-(2-chloro-4-fluorophenyl)-5-(methoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)-2,2-dimethylmorpholine-3-carboxylic acidYield 55%

Procedure

Methyl 6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (6.8 g, 15.3 mmol) was reacted with (S)-2,2-dimethylmorpholine-3-carboxylic acid (2.44 g, 15.3 mmol) according to the procedure as described in Example 46, Step F to give the title compound as a yellow solid (4.4 g, 55%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-92966846706a4efca10e4adac85b5ad4
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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