Trifluoroacetic acid → 4'-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile

HRID 1889346Notes

Reaction equation

COC1C=C(OC)C=CC=1C[N:6]1[C:11](=[O:12])[C:10]2[CH:13]=[C:14]([CH2:16][CH3:17])[S:15][C:9]=2[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:21][CH:20]=2)[C:7]1=[O:33].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH2:16]([C:14]1[S:15][C:9]2[N:8]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:21][CH:20]=3)[C:7](=[O:33])[NH:6][C:11](=[O:12])[C:10]=2[CH:13]=1)[CH3:17]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4′-{[3-(2,4-dimethoxybenzyl)-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (64 g) and trifluoroacetic acid (300 mL) was stirred at 50° C. for 2 hr. To the reaction mixture was added toluene (300 mL), and the mixture was concentrated under reduced pressure. To the obtained residue was added ethyl acetate (150 mL), and the mixture was concentrated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (46.1 g, 100%).

Workup

concentrationthe mixture was concentrated under reduced pressure
additionTo the obtained residue was added ethyl acetate (150 mL)
concentrationthe mixture was concentrated under reduced pressure
filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-340088dca9964eb5861c84b1148a160d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501750B2

Reaction notes

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