Potassium tert-butoxide → 4-Amino-2-[1-(cyclopentyl methyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 1529164Notes

Reaction equation

HRID 1529164 reaction equation
[C:1]([CH:3]([C:11]#[N:12])[C:4]([CH3:10])([CH3:9])[C:5](OC)=[O:6])#[N:2].CC(C)([O-])C.[K+].[CH:19]1([CH2:24][N:25]2[C:29]3=[N:30][CH:31]=[C:32]([F:34])[CH:33]=[C:28]3[C:27]([C:35](=[NH:37])[NH2:36])=[N:26]2)[CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)(C)(C)C>[NH2:2][C:1]1[C:3]2[C:4]([CH3:10])([CH3:9])[C:5](=[O:6])[NH:12][C:11]=2[N:37]=[C:35]([C:27]2[C:28]3[C:29](=[N:30][CH:31]=[C:32]([F:34])[CH:33]=3)[N:25]([CH2:24][CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[N:26]=2)[N:36]=1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 86657403Methyl 3,3-dicyano-2,2-dimethylpropanoateHCID 867151701-(cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

Product 1

HCID 709796024-Amino-2-[1-(cyclopentyl methyl)-5-fluoro-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 6386tert-ButanolSolvent2×

Procedure

30 ml of tert-butanol, 1.068 g (6.429 mmol) of methyl 3,3-dicyano-2,2-dimethylpropanoate dissolved in 15 ml of tert-butanol and 901 mg (8.037 mmol) of potassium tert-butoxide were added to 1.400 g (5.358 mmol) of 1-(cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide, and the mixture was heated under reflux for 24 h. The reaction mixture was concentrated on a rotary evaporator, triturated with 60 ml of water/ethanol (v/v=5:1), filtered off with suction and dried under high vacuum. This gave 1.296 g (57% of theory) of the target compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 h
  3. concentrationThe reaction mixture was concentrated on a rotary evaporator
  4. customtriturated with 60 ml of water/ethanol (v/v=5:1)
  5. filtrationfiltered off with suction
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-bc24e5397b7a4eba92380c21e4e514f1
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

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