Tert-Butylamine → 6'-[2-allyl-6-({4-[(tert-butylamino)methyl]phenyl}amino)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2'-bipyridin-2-one

HRID 2191911

Reaktionsgleichung

Reaktionsgleichung von HRID 2191911
ClCS(O)(=O)=O.[CH2:7]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[N:13][C:14]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27]O)=[CH:23][CH:22]=3)=[N:15][CH:16]=2)[N:11]1[C:29]1[N:34]=[C:33]([N:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]2=[O:41])[CH:32]=[CH:31][CH:30]=1)[CH:8]=[CH2:9].[C:42]([NH2:46])([CH3:45])([CH3:44])[CH3:43].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.O1CCCC1>[CH2:7]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[N:13][C:14]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([CH2:27][NH:46][C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:25][CH:26]=3)=[N:15][CH:16]=2)[N:11]1[C:29]1[N:34]=[C:33]([N:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]2=[O:41])[CH:32]=[CH:31][CH:30]=1)[CH:8]=[CH2:9]

Komponenten

8

Edukt 4

HCID 6385Tert-ButylamineHCID 187807Chloromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 684257146'-[2-allyl-6-{[4-(hydroxymethyl)phenyl]amino}-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2'-bipyridin-2-one

Produkt 1

HCID 426027676'-[2-allyl-6-({4-[(tert-butylamino)methyl]phenyl}amino)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2'-bipyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Chloromethanesulfonic acid (37 μL) was added to a tetrahydrofuran solution (10 mL) of 6′-[2-allyl-6-{[4-(hydroxymethyl)phenyl]amino}-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-2H-1,2′-bipyridin-2-one (110 mg) and triethylamine (164 μL), and stirred at room temperature for 1 hour, then tert-butylamine (500 μL) was added to the reaction liquid, and stirred for 6 hours. Chloroform and aqueous sodium hydrogencarbonate solution were added to the reaction liquid, and the organic layer was separated. The organic layer was washed with saturated saline water, then dried with anhydrous magnesium sulfate, filtered, the solvent was evaporated away, and the resulting crude product was purified through basic silica gel column chromatography (hexane-ethyl acetate/ethanol (19/1) mixture) to give the entitled compound as a white solid substance (9.2 mg).

Aufarbeitung

  1. stirringstirred for 6 hours
  2. customthe organic layer was separated
  3. washThe organic layer was washed with saturated saline water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated away
  7. customthe resulting crude product was purified through basic silica gel column chromatography (hexane-ethyl acetate/ethanol (19/1) mixture)

Quellen und Nachweise

ORD-Eintrag
ord-9e476de24e9940eebec54aafc483b0dd
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329711B2

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