Water → HCID 71539791, compound

HRID 1466211Notes

Reaction equation

HRID 1466211 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:46])([F:45])[C:9]1[CH:10]=[C:11]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1)[CH2:12][NH:13][CH2:14][C:15]1[CH:16]=[C:17]2[C:32]([CH3:33])=[N:31][N:30]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:18]2=[N:19][C:20]=1[N:21]([CH2:26][CH:27]1[CH2:29][CH2:28]1)[CH2:22][CH:23]1[CH2:25][CH2:24]1.[Br:47][C:48]1[CH:49]=[N:50][C:51](Cl)=[N:52][CH:53]=1.O>CN(C=O)C>[F:46][C:8]([F:45])([F:7])[C:9]1[CH:10]=[C:11]([CH:38]=[C:39]([C:41]([F:43])([F:44])[F:42])[CH:40]=1)[CH2:12][N:13]([CH2:14][C:15]1[CH:16]=[C:17]2[C:32]([CH3:33])=[N:31][N:30]([C:34]([CH3:36])([CH3:37])[CH3:35])[C:18]2=[N:19][C:20]=1[N:21]([CH2:26][CH:27]1[CH2:29][CH2:28]1)[CH2:22][CH:23]1[CH2:24][CH2:25]1)[C:51]1[N:52]=[CH:53][C:48]([Br:47])=[CH:49][N:50]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 71539739HCID 71539739, compound

Product 1

HCID 71539791HCID 71539791, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.43 g, 3 mmol) was added to a mixture of 5-(((3,5-bis(trifluoromethyl)benzyl)amino)methyl)-1-(tert-butyl)-N,N-bis(cyclopropylmethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-6-amine (0.6 g, 1 mmol) and 5-bromo-2-chloropyrimidine (0.6 g, 3 mmol) in DMF. The resultant mixture was stirred at 100° C. for 12-16 h. The reaction mixture was treated with water and extracted with ethylacetate (100 ml). The organic layer was washed with brine and dried over Na2SO4, concentrated under reduced pressure to obtain the crude product. This product was further purified by column chromatography using silica gel (60-120 mesh) and 5% ethyl acetate in petroleum ether as eluent.

Workup

  1. extractionextracted with ethylacetate (100 ml)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ebf0a5f377cf43d68d3402281fd23bbf
Source dataset
uspto-grants-2015_04
Patent number
US09000007B2

Reaction notes

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