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

HRID 524563Notes

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[N+:20]([O-:22])=[O:21])[C:4]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH:30]1[C:35]([OH:37])=[O:36].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:26]([O:25][C:23]([C:4]1[CH:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O: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:29]1[CH2:34][CH2:33][O:32][CH2:31][CH:30]1[C:35]([OH:37])=[O:36])=[O:24])[CH3:27]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of ethyl 6-(bromomethyl)-4-(2-nitrophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (2.4 g, 5.3 mmol), morpholine-3-carboxylic acid hydrochloride (0.9 g, 5.37 mmol) and potassium carbonate (1.48 g, 10.74 mmol) in ethanol (60 mL) was stirred at 25° C. for 12 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=25/1) to give the title compound as a light yellow solid (1.1 g, 41%). The compound was characterized by the following spectroscopic data:

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=25/1)

Sources & evidence

ORD record: ord-6efdf8c01f344cccae41d4584938e0fa
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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