Potassium Carbonate → 2-((6-(1-Methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)benzonitrile

HRID 594959Notes

Reaction equation

HRID 594959 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[NH:14][N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1.Br[CH2:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH2:18][C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]#[N:22])[N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 895992-(Bromomethyl)benzonitrileHCID 66765655N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine

Product 1

HCID 671122832-((6-(1-Methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (100 mg, 0.46 mmol), 2-(bromomethyl)benzonitrile (1.1 eq) and potassium carbonate (2 eq) in DMF (2 mL) was stirred at rt for 18 h. The resultant mixture was diluted with EtOAc and washed with H2O, then brine. The organic phase was collected, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography (petroleum ether: EtOAc) to give the title product. 1H NMR (d6-DMSO) δ 9.94 (s, 1H), 8.93 (s, 1H), 8.09 (s, 2H), 7.91 (dd, 1H), 7.67 (td, 1H), 7.51-7.54 (m, 2H), 7.36-7.38 (m, 1H), 5.76 (s, 2H), 3.82 (s, 3H); LC-MS method B, (ES+) 331.0, RT=8.04 min.

Workup

  1. washwashed with H2O
  2. customThe organic phase was collected
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by column chromatography (petroleum ether: EtOAc)

Sources & evidence

ORD record
ord-bfd50f66d886420483e984a6f224fd8f
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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