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 2191911Notes

Reaction equation

HRID 2191911 reaction equation
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]

Participants

8

Reactant 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

Product 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

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-9e476de24e9940eebec54aafc483b0dd
Source dataset
uspto-grants-2012_12
Patent number
US08329711B2

Reaction notes

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