Potassium Carbonate → 4'-[(6-cyclopropyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3'-fluorobiphenyl-2-carbonitrile

HRID 1889360Notes

Reaction equation

HRID 1889360 reaction equation
[CH:1]1([C:4]2[S:25][C:7]3[NH:8][C:9](=[O:24])[N:10](CC4C=CC(OC)=CC=4OC)[C:11](=[O:12])[C:6]=3[CH:5]=2)[CH2:3][CH2:2]1.Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:30][C:29]=1[F:42].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:1]1([C:4]2[S:25][C:7]3[N:8]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([C:34]5[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=5)=[CH:30][C:29]=4[F:42])[C:9](=[O:24])[NH:10][C:11](=[O:12])[C:6]=3[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574600744'-(Bromomethyl)-3'-fluorobiphenyl-2-carbonitrileHCID 593517456-cyclopropyl-3-(2,4-dimethoxybenzyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 593515214'-[(6-cyclopropyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3'-fluorobiphenyl-2-carbonitrileYield 64.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-cyclopropyl-3-(2,4-dimethoxybenzyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (2 g), 4′-(bromomethyl)-3′-fluorobiphenyl-2-carbonitrile (1.8 g), potassium carbonate (1.5 g) and acetonitrile (200 mL) was stirred at 50° C. for 2 hr. Insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in trifluoroacetic acid (50 mL), and the mixture was stirred at 50° C. for 2 hr. To the reaction mixture was added toluene (50 mL), and the mixture was concentrated under reduced pressure. To the obtained residue was added ethyl acetate (50 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 (1.5 g, 64%).

Workup

  1. filtrationInsoluble material was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in trifluoroacetic acid (50 mL)
  4. stirringthe mixture was stirred at 50° C. for 2 hr
  5. additionTo the reaction mixture was added toluene (50 mL)
  6. concentrationthe mixture was concentrated under reduced pressure
  7. additionTo the obtained residue was added ethyl acetate (50 mL)
  8. concentrationthe mixture was concentrated under reduced pressure
  9. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-c461d734e40c4e5a89a3593c87a2dd9a
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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