Potassium Carbonate → 4'-[(6-cyclopropyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3',5'-difluorobiphenyl-2-carbonitrile

HRID 1889384노트

반응식

HRID 1889384 반응식
[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[C:33]([F:34])=[CH:32][C:31]([C:35]2[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=2)=[CH:30][C:29]=1[F:43].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[C:33]([F:34])=[CH:32][C:31]([C:35]5[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=5)=[CH:30][C:29]=4[F:43])[C:9](=[O:24])[NH:10][C:11](=[O:12])[C:6]=3[CH:5]=2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 574605414'-(Bromomethyl)-3',5'-difluorobiphenyl-2-carbonitrileHCID 593517456-cyclopropyl-3-(2,4-dimethoxybenzyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

생성물 1

HCID 593515974'-[(6-cyclopropyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3',5'-difluorobiphenyl-2-carbonitrile수율 94%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

A mixture of 6-cyclopropyl-3-(2,4-dimethoxybenzyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.37 g), 4′-(bromomethyl)-3′,5′-difluorobiphenyl-2-carbonitrile (0.38 g), potassium carbonate (0.29 g) and acetonitrile (30 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 (10 mL), and the mixture was stirred at 50° C. for 2 hr. To the reaction mixture was added toluene (10 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 (0.42 g, 94%).

후처리

  1. filtrationInsoluble material was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in trifluoroacetic acid (10 mL)
  4. stirringthe mixture was stirred at 50° C. for 2 hr
  5. additionTo the reaction mixture was added toluene (10 mL)
  6. concentrationthe mixture was concentrated under reduced pressure
  7. additionTo the obtained residue was added ethyl acetate (10 mL)
  8. concentrationthe mixture was concentrated under reduced pressure
  9. filtrationThe precipitated solid was collected by filtration

출처 및 근거

ORD 기록
ord-61ebecf4c5564f1cbedb0971d5715a58
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501750B2

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