Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate → HCID 90043589, compound

HRID 524834Notes

Reaction equation

HRID 524834 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.[CH3:27][C@@:28]1([C:34]([OH:36])=[O:35])[CH2:33][O:32][CH2:31][CH2:30][NH:29]1>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[N:10]=[C:11]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[NH:12][C:13]([CH2:20][N:29]2[CH2:30][CH2:31][O:32][CH2:33][C@@:28]2([CH3:27])[C:34]([OH:36])=[O:35])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 59495567Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateHCID 90042966HCID 90042966, compound

Product 1

HCID 90043589HCID 90043589, compoundYield 60%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.77 g, 1.53 mmol) was reacted with (S)-3-methylmorpholine-3-carboxylic acid (0.22 g, 1.53 mmol) according to the procedure as described in Example 46, Step F to give the title compound as a yellow solid (0.52 g, 60%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-9bc28fe2e1b94fd2a14005a5ef4a573a
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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