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 536501Notes

Reaction equation

HRID 536501 reaction equation
C[O:2][C:3](=O)[C:4]([CH3:11])([CH3:10])[CH:5]([C:8]#[N:9])[C:6]#[N:7].[F:13][C:14]1[CH:33]=[CH:32][CH:31]=[CH:30][C:15]=1[CH2:16][N:17]1[C:21]2=[N:22][C:23]([CH3:26])=[N:24][CH:25]=[C:20]2[C:19]([C:27](=[NH:29])[NH2:28])=[N:18]1.O>C(O)(C)(C)C>[NH2:7][C:6]1[C:5]2[C:4]([CH3:11])([CH3:10])[C:3](=[O:2])[NH:9][C:8]=2[N:29]=[C:27]([C:19]2[C:20]3[C:21](=[N:22][C:23]([CH3:26])=[N:24][CH:25]=3)[N:17]([CH2:16][C:15]3[CH:30]=[CH:31][CH:32]=[CH:33][C:14]=3[F:13])[N:18]=2)[N:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 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

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

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 h
  3. filtrationthe precipitate was filtered off
  4. extractionThe filtrate was extracted with dichloromethane
  5. dry with materialthe organic phase was dried over sodium sulphate
  6. concentrationconcentrated in a rotary evaporator
  7. additionThe residue was mixed with water/ethanol
  8. filtrationThe solid was filtered off
  9. customdried under high vacuum
  10. custom102 mg (34% of theor.) of the target compound was obtained

Sources & evidence

ORD record
ord-fc1c0437b3354b7e9b84601a0113ed3c
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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