Hydrochloric Acid → 7-(2,4-Dimethoxybenzyl)-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-1,2,3,7-tetrahydropyrido[3,4-d]pyrimidine-4,8-dione

HRID 570731Notes

Reaction equation

[N:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:6][CH:5]=1)=[C:2]=[S:3].[H-].[Na+].[NH2:18][C:19]1[C:20](=[O:41])[N:21]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=2[O:39][CH3:40])[CH:22]=[CH:23][C:24]=1[C:25](OCC)=[O:26].Cl>CN(C)C=O>[CH3:40][O:39][C:32]1[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:31]=1[CH2:30][N:21]1[CH:22]=[CH:23][C:24]2[C:25](=[O:26])[N:1]([C:4]3[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]([F:13])([F:15])[F:14])=[CH:8][CH:9]=3)[C:2](=[S:3])[NH:18][C:19]=2[C:20]1=[O:41]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-isothiocyanato-4-(2,2,2-trifluoroethoxy)benzene (375 mg) in N,N-dimethylformamide (5 ml) was added sodium hydride (60% in oil, 193 mg) under ice-cooling, and the mixture was cooled to 0° C. A solution of ethyl 3-amino-1-(2,4-dimethoxybenzyl)-2-oxo-1,2-dihydropyridine-4-carboxylate (535 mg) in N,N-dimethylformamide (5 ml) was added dropwise thereto, and the mixture was stirred at 0° C. for 15 min. The reaction mixture was poured into 0.3M hydrochloric acid (15 ml), and the precipitate was collected by filtration. The obtained solid was suspended in toluene, and the suspension was concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title compound (527 mg).

Workup

temperaturecooling
filtrationthe precipitate was collected by filtration
concentrationthe suspension was concentrated under reduced pressure
washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record: ord-9845ff307b6347c68c52d540f686e165
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023858B2

Reaction notes

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