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

HRID 1889353Notes

Reaction equation

HRID 1889353 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][C:20]=2[F:33])[C:7]1=[O:34].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][C:20]=3[F:33])[C:7](=[O:34])[NH:6][C:11](=[O:12])[C:10]=2[CH:13]=1)[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593514574'-{[3-(2,4-dimethoxybenzyl)-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}-3'-fluorobiphenyl-2-carbonitrile

Product 1

HCID 593515684'-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3'-fluorobiphenyl-2-carbonitrileYield 100.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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}-3′-fluorobiphenyl-2-carbonitrile (1.3 g) and trifluoroacetic acid (20 mL) was stirred at 50° C. for 2 hr. To the reaction mixture was added toluene (20 mL), and the mixture was concentrated under reduced pressure. To the obtained residue was added ethyl acetate (10 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 (0.95 g, 100%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionTo the obtained residue was added ethyl acetate (10 mL)
  3. concentrationthe mixture was concentrated under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-afebe7a86e344af382f981b40590d896
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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