Water → 6-chloro-1H-pyrazolo[3,4-d]pyrimidine

HRID 876900Notes

Reaction equation

HRID 876900 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]2[NH:9][N:10]=[CH:11][C:3]=12.C(=O)([O-])[O-].[Na+].[Na+].O>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:6]1[N:5]=[C:4]2[NH:9][N:10]=[CH:11][C:3]2=[CH:2][N:7]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 10340Sodium CarbonateHCID 120664494,6-Dichloro-1H-pyrazolo(3,4-d)pyrimidine

Product 1

HCID 529112546-chloro-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

4,6-Dichloro pyrazolo[3,4-d]pyrimidine intermediate 27 and an aryl boronic acid or pinacol ester (1 eq) are suspended in acetonitrile, and sodium carbonate (3 eq, 80 mg) in solution with water. Bis(triphenylphosphine)palladium(II) chloride (0.05 eq) is added. The reaction mixture is heated in microwave at about 80° C. for about 5 min. Water is added to the mixture, and the precipitated product is filtered and purified by column chromatography to yield the 4-aryl, 6-chloro pyrazolo[3,4-d]pyrimidine product 31. Substituents R1′ and R2′ may be R1 and R2 as defined, or protected forms or precursors thereof.

Workup

  1. filtrationthe precipitated product is filtered
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-9eaf502e4b6241aa9ba6db3571ff370a
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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