Potassium Hydroxide → 1-Methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-3-ol

HRID 1351146Notes

Reaction equation

HRID 1351146 reaction equation
C([O:3][C:4]([C:6]1[C:7]([N:14]([CH3:16])[NH2:15])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=O)C.[OH-].[K+]>C(O)(=O)C>[CH3:16][N:14]1[C:7]2=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=[C:6]2[C:4](=[O:3])[NH:15]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 588618224-(N-methyl-hydrazino)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 210980271-Methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-3-olYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(N-Methyl-hydrazino)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (6.0 g, 0.025 mol) was added to a 10% aqueous potassium hydroxide solution. The reaction mixture was heated to reflux for 15 minutes, and then cooled to room temperature. The system was acidified with a 25% aqueous acetic acid solution and the formed product was isolated by filtration. Crude product was recrystalized from a 3:1 ethanol-water mixture to give 4.6 g (95%) of pure 1-methyl-6-methylsulfanyl-1,2-dihydro-pyrazolo[3,4-d]pyrimidin-3-one; LC/MS (m/e)=197.0 (MH+), Rt=1.30 min.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 15 minutes
  3. customthe formed product was isolated by filtration
  4. customCrude product was recrystalized from a 3:1 ethanol-water mixture

Sources & evidence

ORD record
ord-e0e3f700d6254114ae4a8b504936545b
Source dataset
uspto-grants-2007_05
Patent number
US07217710B2

Reaction notes

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