1,2-Dimethoxyethane → 3-(2-Methoxy-5-trifluoromethyl-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

HRID 1396549Notes

Reaction equation

HRID 1396549 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:11])=[N:8][CH:9]=2)[N:4]([CH3:12])[N:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1B(O)O.COCCOC.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.[O-]S([O-])(=O)=O.[Mg+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][C:20]=1[C:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:11])=[N:8][CH:9]=2)[N:4]([CH3:12])[N:3]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27826762-Methoxy-5-(trifluoromethyl)phenylboronic acidHCID 689626923-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine2×

Product 1

HCID 689621693-(2-Methoxy-5-trifluoromethyl-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 24083Sulfuric acid magnesium salt (1:1)Solvent

Procedure

3-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Intermediate 3) (0.1 g, 0.44 mmol), 2-methoxy-5-trifluoromethylphenylboronic acid (0.116 g, 0.53 mmol), Pd(dppf)Cl2 (0.032 g, 0.044 mmol), DME (4 ml) and 2M aqueous Na2CO3, are mixed together and heated using microwave radiation at 100° C. for 30 minutes. The reaction mixture is diluted with EtOAc (30 mls), MgSO4 is added and the resulting mixture is filtered through Celite® (filter agent), washing with EtOAc. The reaction mixture is absorbed onto silica and purification by flash chromatography on silica eluting with DCM then MeOH:DCM (5:95) affords the title compound.

Workup

  1. temperatureheated
  2. customat 100° C.
  3. customfor 30 minutes
  4. additionis added
  5. filtrationthe resulting mixture is filtered through Celite® (filter agent)
  6. washwashing with EtOAc
  7. customThe reaction mixture is absorbed onto silica and purification by flash chromatography on silica eluting with DCM

Sources & evidence

ORD record
ord-00168a93f4b34f7ea02cf3664a97d02f
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

Loading…