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

HRID 1889340Notes

Reaction equation

HRID 1889340 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:11](=[O:12])[C:10]2[CH:13]=[C:14]([CH2:16][C:17]([F:20])([F:19])[F:18])[S:15][C:9]=2[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:24][CH:23]=2)[C:7]1=[O:36].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[O:36]=[C:7]1[N:8]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:26][CH:27]=2)[C:9]2[S:15][C:14]([CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:13][C:10]=2[C:11](=[O:12])[NH:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593515844'-{[3-(2,4-dimethoxybenzyl)-2,4-dioxo-6-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

Product 1

HCID 593517254'-{[2,4-dioxo-6-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrileYield 143.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4′-{[3-(2,4-dimethoxybenzyl)-2,4-dioxo-6-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (1.68 g) and trifluoroacetic acid (30 mL) was stirred at 50° C. for 2 hr. To the reaction mixture was added toluene (30 mL), under reduced pressure, and concentrated. The precipitated solid was collected by filtration to give the title compound as a colorless solid (1.8 g, 100%).

Workup

  1. concentrationunder reduced pressure, and concentrated
  2. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-dfac993cf67942ad802555ea05fb7125
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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