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Triphenylphosphine → 3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 62449
Notes
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Reaction equation

HRID 62449 reaction equation
[S:1]([N:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH:15](O)[C:14]=2[CH:13]=[N:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Br:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[N:28][C:29]=2[NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[O:41][CH3:42])[NH:24][N:23]=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>[Br:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[N:28][C:29]=2[NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[O:41][CH3:42])[N:24]([CH:15]2[CH2:16][CH2:17][CH2:18][C:19]3[N:11]([S:1]([C:4]4[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=4)(=[O:2])=[O:3])[N:12]=[CH:13][C:14]2=3)[N:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 903041681-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-olHCID 178491029HCID 178491029, compound

Product 1

HCID 903039373-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-ol (4.05 g, 11.13 mmol), 3-bromo-N-(2,4-dimethoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (3.9 g, 13.35 mmol) and PPh3 (4.38 g, 16.70 mmol) in dry THF (110 mL) at 0° C. was added dropwise DIAD (3.37 g, 16.70 mmol) over a period of 5 minutes under a nitrogen atmosphere, then the mixture was stirred at room temperature for 4 hours. Removed the solvent under reduced pressure and then extracted with DCM, the combined organic layer was washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo and the residue was purified by preparative HPLC separation to afford 3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.3 g, yield 32.4%). MS-ESI (m/z): 640 (M+2)+ (Acq Method: 10-80AB_2 min; Rt: 1.357 min)

Workup

  1. customRemoved the solvent under reduced pressure
  2. extractionextracted with DCM
  3. washthe combined organic layer was washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was purified by preparative HPLC separation

Sources & evidence

ORD record
ord-5ca6649f5c814447b4fbfc149626ab43
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09446130B2

Reaction notes

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