Triethylamine → ((6-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acid

HRID 524564Notes

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.Cl.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH:29]1[C:34]([OH:36])=[O:35].C(N(CC)CC)C>C(O)C>[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:28]2[CH2:33][CH2:32][O:31][CH2:30][CH:29]2[C:34]([OH:36])=[O:35])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (3.02 g, 6 mmol) (The compound was synthesized according to the procedure as described in WO2010069147A), morpholine-3-carboxylic acid hydrochloride (1 g, 6 mmol) and triethylamine (1.21 g, 12 mmol) in ethanol (40 mL) was stirred at 25° C. for 12 hours under N2. The mixture 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 yellow solid (1.5 g, 45%). The compound was characterized by the following spectroscopic data:

Workup

customwas synthesized
concentrationThe mixture 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-b3da4bf4de9145fb9a37138aabfc3693
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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