Water → N4-(1H-indazol-6-yl)-N2-(4-(methylthio)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

HRID 645686

Reaktionsgleichung

Reaktionsgleichung von HRID 645686
Cl[C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:30]=[C:29]3[C:25]([CH:26]=[N:27][NH:28]3)=[CH:24][CH:23]=2)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[CH3:31][S:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1.C[Si](Cl)(C)C.O>C(O)CCC.C(OCC)(=O)C>[NH:28]1[C:29]2[C:25](=[CH:24][CH:23]=[C:22]([NH:21][C:4]3[C:5]4[CH:10]=[CH:9][N:8]([S:11]([C:14]5[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=5)(=[O:13])=[O:12])[C:6]=4[N:7]=[C:2]([NH:37][C:36]4[CH:38]=[CH:39][C:33]([S:32][CH3:31])=[CH:34][CH:35]=4)[N:3]=3)[CH:30]=2)[CH:26]=[N:27]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 660384-(Methylthio)anilineHCID 866280352-chloro-N-(1H-indazol-6-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Produkt 1

HCID 57585782N4-(1H-indazol-6-yl)-N2-(4-(methylthio)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamineAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
116 °C

Versuchsvorschrift

A mixture of 2-chloro-N-(1H-indazol-6-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (400 mg, 0.912 mmol), 4-(methylthio)aniline (0.227 mL, 1.83 mmol) and trimethylsilyl chloride (TMSCl) (0.231 mL, 1.83 mmol) in n-butyl alcohol (8 mL) was heated at 116° C. for 72 h. Water and ethyl acetate were then added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, and concentrated in vacuo. The residue was dissolved in CH3CN (20 mL), and water was added to induced precipitation. The solid was collected by filtration to give N4-(1H-indazol-6-yl)-N2-(4-(methylthio)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (225 mg). The filtrate was also purified by HPLC to give another portion of the desired product (127 mg).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in CH3CN (20 mL)
  6. additionwater was added to induced precipitation
  7. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-8a6b4e6e18b543378769ec5d14376460
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705004B2

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