HCID 178503501, compound → HCID 178503484, compound

HRID 2114561Notes

Reaction equation

HRID 2114561 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([S:22][CH3:23])=[N:14][C:15]=2[NH:17]C[C@@H](O)C)[NH:10][N:9]=1>N.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([S:22][CH3:23])=[N:14][C:15]=2[NH2:17])[NH:10][N:9]=1

Participants

4

Reactant 1

HCID 178503501HCID 178503501, compound

Product 1

HCID 178503484HCID 178503484, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

200 mg of 4-chloro-3-(2-chloro-phenyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine (from step 4 of Example 1) was dissolved in 5 ml of 7N ammonia in methanol, and the solution was stirred at 80° C. over night in a sealed tube. The resulting reaction mixture was concentrated under vacuum and then extracted in 60 ml ethylacetate. The solution was washed first with water and next with brine, dried and after removing the solvent in vacuo afforded 190 mg (90%)) of 3-(2-chloro-phenyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4ylamine as a light tan solid, MS: 292 (M+H). The crude 3-(2-chloro-phenyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4ylamine was used in the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under vacuum
  3. extractionextracted in 60 ml ethylacetate
  4. washThe solution was washed first with water and next with brine
  5. customdried
  6. customafter removing the solvent in vacuo

Sources & evidence

ORD record
ord-9196fa8e37974dde8d644c7c7066ea8a
Source dataset
uspto-grants-2008_10
Patent number
US07435731B2

Reaction notes

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