Acetone → HCID 15953837, compound

HRID 1818732Notes

Reaction equation

HRID 1818732 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[NH:11][N:12]=[C:13]([NH2:14])[C:8]2=[CH:7][N:6]=1.[CH3:20][C:21]([CH3:23])=O.C1COCC1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCOCC>[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[NH:11][N:12]=[C:13]([NH:14][CH:21]([CH3:23])[CH3:20])[C:8]2=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 178509243HCID 178509243, compound

Product 1

HCID 15953837HCID 15953837, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a room temperature slurry of 6-(2,4-Difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-3-ylamine (170 mg, 0.646 mmol), acetone (0.95 mL, 12.9 mmol) acetic acid (0.037 mL) and THF (6.5 mL) was added NaBH(OAc)3 (547 mg, 2.58 mmol). The reaction mixture was heated to reflux for 18 hours, then cooled to room temperature and diluted with ether. This mixture was washed with water and brine, then dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was chromatographed through silica (10%-50% EtOAc in hexanes) to give 105 mg of [6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-isopropyl-amine, MP=211.3-214.4° C., MS(M+H)=306.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 hours
  3. washThis mixture was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed through silica (10%-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d09fcfa75ce0453d81812c0561b6877a
Source dataset
uspto-grants-2009_10
Patent number
US07601726B2

Reaction notes

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