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Lawesson's reagent → 4-thioxo-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-3,4-dihydro-2(1H)-pyrimidinone hydrochloride

HRID 12782
ノート
印刷プレビュー

反応式

HRID 12782 の反応式
[ClH:1].[F:2][C:3]([F:29])([F:28])[C:4]1[CH:9]=[CH:8][C:7]([C@:10]23[CH2:15][C@H:14]2[CH2:13][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[CH:25]=[CH:24][C:23](=O)[NH:22][C:21]2=[O:27])[CH2:11]3)=[CH:6][CH:5]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>COCCOC>[ClH:1].[S:39]=[C:23]1[CH:24]=[CH:25][N:20]([CH2:19][CH2:18][CH2:17][CH2:16][N:12]2[CH2:13][C@H:14]3[C@:10]([C:7]4[CH:8]=[CH:9][C:4]([C:3]([F:29])([F:28])[F:2])=[CH:5][CH:6]=4)([CH2:15]3)[CH2:11]2)[C:21](=[O:27])[NH:22]1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 686914601-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione hydrochloride

生成物 1

HCID 866159544-thioxo-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-3,4-dihydro-2(1H)-pyrimidinone hydrochloride収率 63%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of 1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione (E5, 110 mg, 0.3 mmol) and Lawesson's reagent (184 mg, 0.5 mmol) in DME (2 mL) was stirred at reflux for 2 hours. The solvent was evaporated under vacuum. The crude was re-dissolved in ethyl acetate and washed with water. The organic phase was dried (Na2SO4) filtered and evaporated; the crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2) to give the title compound as a yellow oil (80 mg, 63% yield).

後処理

  1. temperatureat reflux for 2 hours
  2. customThe solvent was evaporated under vacuum
  3. dissolutionThe crude was re-dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customthe crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2)

出典と根拠

ORDレコード
ord-fb66b91e750f4f81a06e92bdd42c658d
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07727988B2

反応ノート

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