Dimethylformamide → 5,5-Dimethyl-1-(2-((4-(3-(trifluoromethyl)-2-thienyl)-2-pyrimidinyl)amino)ethyl)-2,4-imidazolidinedione

HRID 507629ノート

反応式

HRID 507629 の反応式
I[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][N:16]2[C:20]([CH3:22])([CH3:21])[C:19](=[O:23])[NH:18][C:17]2=[O:24])[N:8]=1.[F-].[K+].C([Si](CC)(CC)[C:30]([F:33])([F:32])[F:31])C.CN(C=O)C>ClCCl.[Cu]I.CN1C(=O)CCC1>[CH3:21][C:20]1([CH3:22])[N:16]([CH2:15][CH2:14][NH:13][C:9]2[N:8]=[C:7]([C:3]3[S:4][CH:5]=[CH:6][C:2]=3[C:30]([F:33])([F:32])[F:31])[CH:12]=[CH:11][N:10]=2)[C:17](=[O:24])[NH:18][C:19]1=[O:23]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 4204914Triethyl(trifluoromethyl)silaneHCID 602045261-(2-(4-(3-Iodothiophen-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione

生成物 1

HCID 602045345,5-Dimethyl-1-(2-((4-(3-(trifluoromethyl)-2-thienyl)-2-pyrimidinyl)amino)ethyl)-2,4-imidazolidinedione

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6344Dichloromethane溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

A sealed tube charged with 1-(2-(4-(3-iodothiophen-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (0.300 g, 0.656 mmol), copper (I) iodide (0.275 g, 1.44 mmol), spray-dried potassium fluoride (0.075 g, 1.3 mmol), triethyl(trifluoromethyl)silane (0.25 mL, 1.3 mmol), DMF (1.0 mL), and NMP (1.0 mL) was heated to 80° C. and allowed to stir for 72 h. At that time, the mixture was diluted with 20 mL dichloromethane and filtered. The pale green filtrate was then purified through Celite and the plug was washed with 10% MeOH/dichloromethane and H2O. The organic solvents were removed from the biphasic mixture in vacuo and the aqueous residue was then partitioned between dichloromethane and H2O. The organic phase was separated, concentrated and the residue purified by flash chromatography, eluting with 1-6% MeOH/dichloromethane to afford the product as a white solid. MS (M+H)+ 400.

後処理

  1. filtrationfiltered
  2. customThe pale green filtrate was then purified through Celite
  3. washthe plug was washed with 10% MeOH/dichloromethane and H2O
  4. customThe organic solvents were removed from the biphasic mixture in vacuo
  5. customthe aqueous residue was then partitioned between dichloromethane and H2O
  6. customThe organic phase was separated
  7. concentrationconcentrated
  8. customthe residue purified by flash chromatography
  9. washeluting with 1-6% MeOH/dichloromethane

出典と根拠

ORDレコード
ord-b3b869a29ec441f3b0e45bb47b634c59
出典データセット
uspto-grants-2010_08
特許番号
US07786132B2

反応ノート

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