2-Bromopropane → HCID 68802502, compound

HRID 229404Notes

Reaction equation

HRID 229404 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[N:15][CH:16]=[C:11]2[C:10]([OH:26])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH:33](Br)([CH3:35])[CH3:34]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[N:15][CH:16]=[C:11]2[C:10]([O:26][CH:33]([CH3:35])[CH3:34])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178452560HCID 178452560, compound

Product 1

HCID 68802502HCID 68802502, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

6-(2,4-Difluoro-phenoxy)-3-hydroxy-pyrazolo[3,4-d]pyrimidine-1-carboxylic acid tert-butyl ester (190 mg, 0.52 mmol) was mixed with K2CO3 (144 mg, 1 mmol) and isopropyl bromide (0.29 mL, 5.2 mmol) in DMF (3 mL). The mixture was heated at 40° C. for 4 hours, then cooled and diluted with water. The resulting mixture was extracted with EtOAc and the combined organic fractions were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified with flash column chromatography flushing with 30% ethyl acetate in hexanes to give 190 mg of 6-(2,4-difluoro-phenoxy)-3-isopropoxy-pyrazolo[3,4-d]pyrimidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperaturecooled
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialthe combined organic fractions were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with flash column chromatography
  7. customflushing with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a0d4604610654a509763c90de2d0b929
Source dataset
uspto-grants-2009_07
Patent number
US07563800B2

Reaction notes

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