Toluene → 4-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1931606Notes

Reaction equation

HRID 1931606 reaction equation
C([SiH](CC)CC)C.[CH3:8][S:9]([C:12]1[CH:33]=[CH:32][C:15]([O:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[N:23](C4CCCCO4)[N:24]=[CH:25][C:18]=23)=[CH:14][CH:13]=1)(=[O:11])=[O:10].FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[CH3:8][S:9]([C:12]1[CH:33]=[CH:32][C:15]([O:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[NH:23][N:24]=[CH:25][C:18]=23)=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 669152954-(4-methanesulfonyl-phenoxy)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 579650144-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidineYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylsilane (150 μL, 0.94 mmol) was added to a solution of 4-(4-methanesulfonyl-phenoxy)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine (150 mg, 0.4 mmol) in dichloromethane (3 mL). A solution of trifluoroacetic acid (1 mL) in dichloromethane (3 mL) was added dropwise and then the reaction mixture was stirred for 1 h. Toluene (2 mL) was added and the volatiles were evaporated. The residue was purified by column chromatography, eluting with 0-5% methanol/ethyl acetate to give 4-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine (71 mg, 61%) as a white solid.

Workup

  1. customthe volatiles were evaporated
  2. customThe residue was purified by column chromatography
  3. washeluting with 0-5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-363ad5bc919840ac9e1fac663180592c
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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