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

HRID 507629노트

반응식

HRID 507629 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6344Dichloromethane용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b3b869a29ec441f3b0e45bb47b634c59
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786132B2

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