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

HRID 1889430Notes

Reaction equation

HRID 1889430 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[NH:8][C:7]1=[O:18].Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[C:34]([C:39]#[N:40])=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:29]([F:41])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:16]([C:14]1[S:15][C:9]2[N:8]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]4[C:34]([C:39]#[N:40])=[CH:35][CH:36]=[CH:37][CH:38]=4)=[C:29]([F:41])[CH:28]=3)[C:7](=[O:18])[NH:6][C:11](=[O:12])[C:10]=2[CH:13]=1)[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 593517753-(2,4-dimethoxybenzyl)-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneHCID 670084324'-(Bromomethyl)-2'-fluorobiphenyl-2-carbonitrile

Product 1

HCID 593517974'-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-2'-fluorobiphenyl-2-carbonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-(2,4-dimethoxybenzyl)-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (2 g), 4′-(bromomethyl)-2′-fluorobiphenyl-2-carbonitrile (2 g), potassium carbonate (1.6 g) and acetonitrile (40 mL) was stirred at 50° C. for 1.5 hr. Insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in trifluoroacetic acid (15 mL), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was concentrated under reduced pressure. To the obtained residue was added ethyl acetate, and insoluble material was filtered off. The filtrate was concentrated and recrystallized from diethyl ether to give the title compound as a colorless solid (1.6 g, 90%).

Workup

  1. filtrationInsoluble material was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in trifluoroacetic acid (15 mL)
  4. stirringthe mixture was stirred at 50° C. for 2 hr
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additionTo the obtained residue was added ethyl acetate, and insoluble material
  7. filtrationwas filtered off
  8. concentrationThe filtrate was concentrated
  9. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-b7197d1f00d54848a3628ef762cdfe4a
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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