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

HRID 570527Notes

Reaction equation

HRID 570527 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 were dissolved in 15 ml of absolute methanol. 209 mg (3.72 mmol) of sodium methoxide were added and the mixture was stirred at RT for 1 h. Subsequently, 31 mg (0.56 mmol) of sodium methoxide were added and the mixture was stirred at RT for 15 min. 871 mg (14.50 mmol) of acetic acid and 489 mg (4.46 mmol) of ammonium chloride were added and the mixture was stirred at 45° C. for 45 min. The reaction mixture was concentrated, the residue was stirred with 1N sodium hydroxide solution, and the precipitate was filtered off with suction and dried under high vacuum. 918 mg (purity 91%, 97% of theory) of the target compound were obtained.

Workup

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

Sources & evidence

ORD record
ord-cd12311dfdf948eaa38d822015dd36c4
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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