Potassium Carbonate → HCID 68893929, compound

HRID 1396544Notes

Reaction equation

HRID 1396544 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7]2[N:9]([CH3:21])[N:10]=[C:11]([C:12]3[CH:17]=[C:16]([F:18])[C:15]([OH:19])=[C:14]([Br:20])[CH:13]=3)[C:6]2=[CH:5][N:4]=1.C([O-])([O-])=O.[K+].[K+].[CH3:28][O:29][CH2:30][CH2:31]Br>CN(C=O)C.CO>[Br:20][C:14]1[CH:13]=[C:12]([C:11]2[C:6]3[C:7](=[N:8][C:3]([NH2:2])=[N:4][CH:5]=3)[N:9]([CH3:21])[N:10]=2)[CH:17]=[C:16]([F:18])[C:15]=1[O:19][CH2:31][CH2:30][O:29][CH3:28]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 136387218HCID 136387218, compound

Product 1

HCID 68893929HCID 68893929, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4-(6-Amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-bromo-6-fluoro-phenol hydrochloride (Example 42b) (30 mg, 0.08 mmol) is dissolved in DMF (1 ml) then treated with K2CO3 (24 mg, 0.18 mmol) and 2-bromoethyl methyl ether (7.5 μL, 0.08 mmol). The reaction mixture is heated at 120° C. for 3 hours then cooled to room temperature, diluted with MeOH and concentrated in vacuo. The crude residue is dry loaded onto silica and purification by flash chromatography on silica eluting with iso-hexanes:EtOAc (50% EtOAc to 100% EtOAc) affords the title compound as an off-white soild.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dry with materialThe crude residue is dry loaded onto silica and purification by flash chromatography on silica eluting with iso-hexanes

Sources & evidence

ORD record
ord-040042a6d5e64c0ebb754996eb660171
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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