Water → 4-Amino-2-[1-(2-fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 570528Notes

Reaction equation

HRID 570528 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15](=[NH:17])[NH2:16])=[N:6]1.[C:22]([CH:24]([C:32]#[N:33])[C:25]([CH3:31])([CH3:30])[C:26](OC)=[O:27])#[N:23].CC(C)([O-])C.[K+].O>C(O)(C)(C)C>[NH2:23][C:22]1[C:24]2[C:25]([CH3:31])([CH3:30])[C:26](=[O:27])[NH:33][C:32]=2[N:17]=[C:15]([C:7]2[C:8]3[C:9](=[N:10][C:11]([CH3:14])=[N:12][CH:13]=3)[N:5]([CH2:4][C:3]3[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=3[F:1])[N:6]=2)[N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86657403Methyl 3,3-dicyano-2,2-dimethylpropanoateHCID 866920951-(2-Fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide

Product 1

HCID 712856424-Amino-2-[1-(2-fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

200 mg (0.70 mmol) of 1-(2-fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide were admixed with 3 ml of tert-butanol, 146 mg (0.70 mmol) of methyl 3,3-dicyano-2,2-dimethylpropanoate dissolved in 1.5 ml of tert-butanol and 94 mg (0.84 mmol) of potassium tert-butoxide, and the mixture was heated under reflux for 48 h. Water was added and the precipitate was filtered off. The filtrate was extracted with dichloromethane, and the organic phase was dried over sodium sulphate and concentrated on a rotary evaporator. The residue was stirred with water/ethanol. The solid was filtered off and dried under high vacuum. 102 mg (34% of theory) of the target compound were obtained.

Workup

  1. temperatureunder reflux for 48 h
  2. filtrationthe precipitate was filtered off
  3. extractionThe filtrate was extracted with dichloromethane
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. concentrationconcentrated on a rotary evaporator
  6. filtrationThe solid was filtered off
  7. customdried under high vacuum
  8. custom102 mg (34% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-dfcc7c75834148b383cbf324c66272fa
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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