Cesium carbonate → 4-(2-(4-(4-methyl-1-phenyl-1H-pyrazol-3-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-amine

HRID 252645Notes

Reaction equation

HRID 252645 reaction equation
[CH3:1][C:2]1[C:3]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1.Cl[C:22]1[C:27]([C:28]2[CH:33]=[CH:32][N:31]=[C:30]([NH2:34])[N:29]=2)=[CH:26][CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:1][C:2]1[C:3]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:22]3[C:27]([C:28]4[CH:33]=[CH:32][N:31]=[C:30]([NH2:34])[N:29]=4)=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:18][CH:19]=2)=[N:4][N:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 533963354-(2-Chloropyridin-3-yl)pyrimidin-2-amineHCID 668633924-(4-methyl-1-phenyl-1H-pyrazol-3-ylamino)phenol

Product 1

HCID 249834704-(2-(4-(4-methyl-1-phenyl-1H-pyrazol-3-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
130 °C

Procedure

A resealable reaction tube was charged with 4-(4-methyl-1-phenyl-1H-pyrazol-3-ylamino)phenol (0.12 g, 0.45 mmol), 4-(2-chloropyridin-3-yl)pyrimidin-2-amine (0.09 g, 0.45 mmol), cesium carbonate (0.30 g, 0.91 mmol), and DMSO (2.26 ml, 0.2 M). The reaction vessel was sealed and the mixture stirred at 130° C. for 16 h. The reaction was cooled to RT, diluted with 1 ml DMSO and passed through a PTFE acrodisc filter via syringe. The residue was purified by Gilson reverse phase chromatography (10% to 90% CH3CN/H2O/0.1% TFA), and the product-containing fractions were combined, basified by addition of aq. NaHCO3 and extracted with ethyl acetate. The organic portion was dried with Na2SO4, filtered, and concentrated to afford pure 4-(2-(4-(4-methyl-1-phenyl-1H-pyrazol-3-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-amine as a tan solid. MS m/z=436.2 [M+H]+. Calc'd for C25H21N7O: 435.48.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was cooled to RT
  3. filtrationacrodisc filter via syringe
  4. customThe residue was purified by Gilson reverse phase chromatography (10% to 90% CH3CN/H2O/0.1% TFA)
  5. additionbasified by addition of aq. NaHCO3
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic portion was dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e9b7030cb4a4404eb74b3dd01fbc54c8
Source dataset
uspto-grants-2011_01
Patent number
US07868177B2

Reaction notes

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