Acetic Acid → 1-(2-Fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide

HRID 536500Notes

Reaction equation

HRID 536500 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][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]#[N:16])=[N:6]1.C[O-].[Na+].C(O)(=O)C.[Cl-].[NH4+:29]>CO>[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][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:29])[NH2:16])=[N:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide2×HCID 712856751-(2-Fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile

Product 1

HCID 866920951-(2-Fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under an argon atmosphere, 994 mg (purity 81%, approx. 3.01 mmol) of 1-(2-fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile was dissolved in 15 ml of absolute methanol. 209 mg (3.72 mmol) of sodium methylate was added and it was stirred for 1 h at RT. Then a further 31 mg (0.56 mmol) of sodium methylate was added and it was stirred for 15 min at RT. 871 mg (14.50 mmol) of acetic acid and 489 mg (4.46 mmol) of ammonium chloride were added and the mixture was stirred for 45 min at 45° C. The reaction mixture was concentrated by evaporation, the residue was mixed with 1N sodium hydroxide solution, the precipitate was filtered with suction and dried under high vacuum. 918 mg (purity 91%, 97% of theor.) of the target compound was obtained.

Workup

  1. stirringit was stirred for 15 min at RT
  2. stirringthe mixture was stirred for 45 min at 45° C
  3. concentrationThe reaction mixture was concentrated by evaporation
  4. additionthe residue was mixed with 1N sodium hydroxide solution
  5. filtrationthe precipitate was filtered with suction
  6. customdried under high vacuum
  7. custom918 mg (purity 91%, 97% of theor.) of the target compound was obtained

Sources & evidence

ORD record
ord-1f2d7c33440445d8bb236cd4400d223b
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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