Triphenylphosphine → 3-iodo-1-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 62441Notes

Reaction equation

HRID 62441 reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6](O)[C:5]=2[CH:4]=[N:3]1.[I:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[N:19][C:20]=2[NH2:22])[NH:15][N:14]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[I:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[N:19][C:20]=2[NH2:22])[N:15]([CH:6]2[CH2:7][CH2:8][CH2:9][C:10]3[N:2]([CH3:1])[N:3]=[CH:4][C:5]2=3)[N:14]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 138368981-methyl-4,5,6,7-tetrahydro-1H-indazol-4-olHCID 178508725HCID 178508725, compound

Product 1

HCID 903040593-iodo-1-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ol (400 mg, 2.63 mmol) and 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (684 mg, 2.63 mmol) and Ph3P (1.03 g, 3.94 mmol) in THF (40 mL) was added DIAD (798 mg, 3.94 mmol) dropwise at 0° C. After the addition was completed, the mixture was allowed to warm to room temperature and stirred for 3 hours. The mixture was extracted with EA, the combined the organic layers were washed with brine and dried over anhydrous Na2SO4. The volatiles were concentrated in vacuo and the residue was purified by silica gel chromatography (DCM/methanol=40/1 v/v %) to give 3-iodo-1-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (80 mg, 8%). MS-ESI (m/z): 396 (M+1)+ (Acq Method: 10-80AB_2 min_220 &254.1 cm; Rt: 0.82 min)

Workup

  1. additionAfter the addition
  2. extractionThe mixture was extracted with EA
  3. washwere washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe volatiles were concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (DCM/methanol=40/1 v/v %)

Sources & evidence

ORD record
ord-96e198c0defd457ea4756ab3e0a39bbc
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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