Sodium ethoxide → HCID 68015337, compound

HRID 570734Notes

Reaction equation

C(S[C:5]1[N:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:19][CH:18]=2)[C:7](=[O:16])[C:8]2[CH:14]=[CH:13][NH:12][C:11](=[O:15])[C:9]=2[N:10]=1)CC.[O-:29][CH2:30][CH3:31].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[CH2:30]([O:29][C:5]1[N:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:27])([F:28])[F:26])=[CH:19][CH:18]=2)[C:7](=[O:16])[C:8]2[CH:14]=[CH:13][NH:12][C:11](=[O:15])[C:9]=2[N:10]=1)[CH3:31]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,7-dihydropyrido[3,4-d]pyrimidine-4,8-dione (535 mg) in N,N-dimethylformamide (5 ml) was added sodium ethoxide (20% ethanol solution, 0.863 ml), and the mixture was stirred at 60° C. for 4 hr. The reaction mixture was allowed to be cooled to room temperature, saturated brine was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (140 mg).

Workup

temperatureto be cooled to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)

Sources & evidence

ORD record: ord-2c8e5daa217e49b497b633125099faa8
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023858B2

Reaction notes

Loading…