Hydrochloric Acid → 4-(3-Aminopyrrolidin-1-yl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 536531Notes

Reaction equation

HRID 536531 reaction equation
Cl.C(OC(=O)[NH:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[C:39]([CH3:41])([CH3:40])[C:38](=[O:42])[NH:37][C:16]=3[N:17]=[C:18]([C:20]3[C:28]4[C:23](=[N:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[F:36])[N:21]=3)[N:19]=2)[CH2:10]1)(C)(C)C>C(OCC)C>[NH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[C:39]([CH3:40])([CH3:41])[C:38](=[O:42])[NH:37][C:16]=3[N:17]=[C:18]([C:20]3[C:28]4[C:23](=[N:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[F:36])[N:21]=3)[N:19]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71290251tert.-Butyl-(1-{2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}pyrrolidin-3-yl)carbamate

Product 1

HCID 712858064-(3-Aminopyrrolidin-1-yl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.71 ml of a 2N solution of hydrogen chloride in diethyl ether was added to 81 mg (0.24 mmol) of tert.-butyl-(1-{2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}pyrrolidin-3-yl)carbamate (racemate, example 61A) and it was stirred for 4 h at room temperature. The reaction solution was concentrated and was purified by preparative HPLC (acetonitrile/water (+0.1% trifluoroacetic acid) gradient). The concentrated fractions were dissolved in dichloromethane and washed twice with saturated aqueous sodium hydrogen carbonate solution. The combined aqueous phases were extracted twice with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered and concentrated by evaporation. 37 mg (55% of theor.) of the target compound was obtained.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customwas purified by preparative HPLC (acetonitrile/water (+0.1% trifluoroacetic acid) gradient)
  3. dissolutionThe concentrated fractions were dissolved in dichloromethane
  4. washwashed twice with saturated aqueous sodium hydrogen carbonate solution
  5. extractionThe combined aqueous phases were extracted twice with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. custom37 mg (55% of theor.) of the target compound was obtained

Sources & evidence

ORD record
ord-9aa896a355e6499aa10788a76399b6b4
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

Loading…