Potassium Carbonate → 4-(3-aminophenoxy)-N-{1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 577670Notes

Reaction equation

HRID 577670 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[O:5][C:6]1[C:7]2[CH:25]=[CH:24][N:23](CO)[C:8]=2[N:9]=[C:10]([NH:12][C:13]2[CH:14]=[N:15][N:16]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[CH:17]=2)[N:11]=1.C([O-])([O-])=O.[K+].[K+]>CO.O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[O:5][C:6]1[C:7]2[CH:25]=[CH:24][NH:23][C:8]=2[N:9]=[C:10]([NH:12][C:13]2[CH:14]=[N:15][N:16]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[CH:17]=2)[N:11]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86679613[4-(3-aminophenoxy)-2-({1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methanol

Product 1

HCID 866796154-(3-aminophenoxy)-N-{1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of [4-(3-aminophenoxy)-2-({1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methanol in MeOH (10 mL) and water (2 mL) was added K2CO3 until the pH of the reaction mixture was about 12. The reaction mixture was then stirred at rt for 2 hrs. Water was added and extracted with EtOAc (three×20 mL), dried with MgSO4, filtered and stripped to a dark oil to give the title compound as a dark oil that was taken on to the next step with no purification. m/z (ESI+) for C19H22N8O 379.15 (M+H)+.

Workup

  1. extractionextracted with EtOAc (three×20 mL)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered

Sources & evidence

ORD record
ord-37fd9e2c6c46437e8dd79514e84396b9
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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