Potassium Carbonate → HCID 59351756, compound

HRID 1889399Notes

Reaction equation

HRID 1889399 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:11](=[O:12])[C:10]2[CH:13]=[C:14]([CH2:16][CH2:17][CH3:18])[S:15][C:9]=2[NH:8][C:7]1=[O:19].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>[O:19]=[C:7]1[N:8]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:30][C:29]=2[F:42])[C:9]2[S:15][C:14]([CH2:16][CH2:17][CH3:18])=[CH:13][C:10]=2[C:11](=[O:12])[NH:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574600744'-(Bromomethyl)-3'-fluorobiphenyl-2-carbonitrileHCID 59351515HCID 59351515, compound

Product 1

HCID 59351756HCID 59351756, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-(2,4-dimethoxybenzyl)-6-propylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (2.7 g), 4′-(bromomethyl)-3′-fluorobiphenyl-2-carbonitrile (2.6 g), potassium carbonate (2.1 g) and acetonitrile (100 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 (2 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-1998acc0acbb4159bcf2983f3f807de8
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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