Potassium Carbonate → 4-((5-(Ethoxycarbonyl)-2-(thiazol-2-yl)-6-(2-(trifluoromethyl)phenyl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acid

HRID 524560Notes

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][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])[C:4]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].Cl.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH:31]1[C:36]([OH:38])=[O:37].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:27]([O:26][C:24]([C:4]1[CH:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])[N:6]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[NH:8][C:3]=1[CH2:2][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH:31]1[C:36]([OH:38])=[O:37])=[O:25])[CH3:28]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of ethyl 6-(bromomethyl)-2-(thiazol-2-yl)-4-(2-(trifluoromethyl)phenyl)-1,4-dihydropyrimidine-5-carboxylate (3.8 g, 8 mmol), morpholine-3-carboxylic acid hydrochloride (2.62 g, 16 mmol) and potassium carbonate (4.2 g, 30 mmol) in ethanol (130 mL) was stirred at 25° C. for 12 hours. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=30/1) to give the title compound as a yellow solid (2.1 g, 50%). The compound was characterized by the following spectroscopic data:

Workup

filtrationThe resulting mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=30/1)

Sources & evidence

ORD record: ord-d596c1d4d10842d193154eba0b1eea19
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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