Formamide → 3-Methyl-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2426103Notes

Reaction equation

HRID 2426103 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH3:7])[C:3]=1[C:8]([NH2:10])=[O:9].[CH:11](N)=O>O>[CH3:7][C:4]1[N:5]=[N:6][C:2]2[C:3]=1[C:8](=[O:9])[N:10]=[CH:11][N:1]=2

Participants

4

Reactant 2

HCID 713FormamideHCID 178434679HCID 178434679, compound

Product 1

HCID 536298293-Methyl-pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 5-amino-3-methyl-1H-pyrazole-4-carboxylic acid amide (11.06 g, 79.0 mmol, Example 1) and formamide (60 mL, Aldrich) was heated at 180° C. for 3.5 hours. After cooling to 80° C., icy water (100 g) was added and the mixture was vigorously stirred to give a white precipitate. The precipitate was filtered and washed with cold water and then dried in a vacuum desiccator to give 3-methyl-pyrazolo[3,4-d]pyrimidin-4-one as an off-white solid. (Yield 9.07 g). This material was used in the next step (described in Example 3) without further purification.

Workup

  1. temperatureAfter cooling to 80° C.
  2. customto give a white precipitate
  3. filtrationThe precipitate was filtered
  4. washwashed with cold water
  5. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-2c280aba1dff432fa3eeeefe03d6a234
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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