Water → HCID 46830431, compound

HRID 2194471Notes

Reaction equation

HRID 2194471 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[N:15]=[C:14]([NH2:16])[C:13]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[CH:12][N:11]=2)=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:29]1([CH2:35]Br)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.O>CN(C=O)C>[CH:29]1([CH2:35][N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[C:3]([C:10]3[N:15]=[C:14]([NH2:16])[C:13]([C:17]4[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=4)=[CH:12][N:11]=3)=[N:2]2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 178508328HCID 178508328, compound

Product 1

HCID 46830431HCID 46830431, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg (0.691 mmol) of 2-(1H-pyrazolo[3,4-b]pyridin-3-yl)-5-(pyridin-4-yl)pyrimidine-4-amine (preparation: see WO 03/097063, Example 35A) were dissolved in 5 ml of DMF, and 248 mg (0.760 mmol) of cesium carbonate and 136 mg (0.760 mmol) of cyclohexylmethyl bromide were added. The mixture was stirred at RT overnight. Water was added, and the mixture was extracted three times with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated on a rotary evaporator. The residue was fractionated by preparative HPLC (Method 5). The product-containing fractions were combined and concentrated on a rotary evaporator, and the residue was dried under high vacuum. This gave 29 mg (11% of theory) of the target compound.

Workup

  1. extractionthe mixture was extracted three times with dichloromethane
  2. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. concentrationconcentrated on a rotary evaporator
  6. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-ecd5d6fb96ef4d13a6d7daad59af9cc1
Source dataset
uspto-grants-2012_12
Patent number
US08334291B2

Reaction notes

Loading…