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

HRID 1889430ノート

反応式

HRID 1889430 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b7197d1f00d54848a3628ef762cdfe4a
出典データセット
uspto-grants-2013_08
特許番号
US08501750B2

反応ノート

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