Ethanol → Ethyl 6-[(2,2-diphenylethyl)amino]-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carboxylate

HRID 10465

反応式

HRID 10465 の反応式
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([NH:17][CH2:18][CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1.[C:32](=[O:35])([O-])[O-:33].[Na+].[Na+].[CH2:38](O)[CH3:39]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:20]1([CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:18][NH:17][C:4]2[N:3]=[C:2]([C:32]([O:33][CH2:38][CH3:39])=[O:35])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 3

HCID 702Ethanol2 回HCID 10340Sodium CarbonateHCID 101813352-Chloro-N-(2,2-diphenylethyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

生成物 1

HCID 21978293Ethyl 6-[(2,2-diphenylethyl)amino]-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carboxylate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒

反応条件

温度
60 °C

実験手順

To a suspension of palladium (II) acetate (1.50 g, 0.00668 moles) in absolute ethanol (1000 ml) was added 1,1′-bis(diphenylphosphino)ferrocene (7.00 g, 0.0126 moles) and the resultant suspension was stirred under an atmosphere of nitrogen for 18 hours to give the catalyst mixture. To a mixture of 2-chloro-N-(2,2-diphenylethyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (WO/0023457) (Preparation 2) (700 g, 1.61 moles) and absolute ethanol (4500 ml) in an autoclave was added anhydrous sodium carbonate (94 g, 0.887 moles) and the catalyst mixture prepared above. The autoclave was flushed twice with carbon monoxide gas, then pressurised to 2000 kPa using carbon monoxide gas. The mixture was then heated at 103–107° C. with stirring for 10 hours, and the autoclave was then vented, flushed with carbon monoxide, and then re-pressurised to 2000 kPa with carbon monoxide. Heating at 103–107° C. with stirring was continued for a further 14 hours. The mixture was cooled to 60° C. and then filtered through a bed of warm Celite (trade mark). The resultant filtrate was allowed to cool to ambient temperature whereupon crystallisation occurred and, after stirring at this temperature for 7 hours, the resultant suspension was filtered The filter cake was washed with cold absolute ethanol (500 ml) and the solid was dried in vacuo for 24 hours at 55° C. to give the title compound as a cream coloured solid (575 g), m.p. 138–140° C.

後処理

  1. customto give the catalyst mixture
  2. customthe catalyst mixture prepared above
  3. customThe autoclave was flushed twice with carbon monoxide gas
  4. temperatureThe mixture was then heated at 103–107° C.
  5. customflushed with carbon monoxide
  6. temperatureHeating at 103–107° C.
  7. stirringwith stirring
  8. waitwas continued for a further 14 hours
  9. filtrationfiltered through a bed of warm Celite (trade mark)
  10. temperatureto cool to ambient temperature whereupon crystallisation
  11. stirringafter stirring at this temperature for 7 hours
  12. filtrationthe resultant suspension was filtered The filter cake
  13. washwas washed with cold absolute ethanol (500 ml)
  14. customthe solid was dried in vacuo for 24 hours at 55° C.

出典と根拠

ORDレコード
ord-511b94495bbc4410b949c19d4a59e5c2
出典データセット
uspto-grants-2006_08
特許番号
US07094769B2

関連ノート

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