2-Bromoethanol → HCID 68893344, compound

HRID 1396545Notes

Reaction equation

HRID 1396545 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+].Br[CH2:29][CH2:30][OH:31]>CN(C=O)C.CO>[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]([O:19][CH2:29][CH2:30][OH:31])=[C:14]([Br:20])[CH:13]=3)[C:6]2=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 136387218HCID 136387218, compound

Product 1

HCID 68893344HCID 68893344, 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-bromoethanol (5.7 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 onto silica. Purification by flash column chromatography on silica using iso-hexanes:EtOAc (50% EtOAc to 100% EtOAc) followed by recrystallisation from MeOH afforded the title compound as an off-white solid.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated onto silica
  3. customPurification by flash column chromatography on silica
  4. customEtOAc (50% EtOAc to 100% EtOAc) followed by recrystallisation from MeOH

Sources & evidence

ORD record
ord-bb39ec38767d48b9ae4e3de6466fe450
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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