Acetone → 4-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butane-1,2-diol

HRID 2357982Notes

Reaction equation

HRID 2357982 reaction equation
[CH2:1]([N:5]1[C:9]2=[N:10][C:11]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:12][CH:13]=[C:8]2[C:7]([NH:21][C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:29])=[N:6]1)CC=C.[NH+]1([O-])CC[O:33]CC1.[CH3:37][C:38]([CH3:40])=[O:39]>O.O=[Os](=O)(=O)=O>[CH3:29][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([CH3:28])[C:22]=1[NH:21][C:7]1[C:8]2[C:9](=[N:10][C:11]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:12][CH:13]=2)[N:5]([CH2:1][CH2:37][CH:38]([OH:39])[CH2:40][OH:33])[N:6]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 15900019Morpholine oxideHCID 160487521-(but-3-enyl)-N3-(2,6-dimethylphenyl)-N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine

Product 1

HCID 160488204-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butane-1,2-diol

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 363 mg (0.9 mmol) of 1-(but-3-enyl)-N3-(2,6-dimethylphenyl)-N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine 33 (Example 1, Step D) and a catalytic amount of OsO4 in 28.5 mL acetone and 10 mL water was treated with 400 mg (97%, 3.3 mmol) of morpholine-N-oxide. The resulting yellow solution was stirred at room temperature for 18 h. The reaction mixture was diluted with water (95 mL) and extracted with CH2Cl2 (3×240 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 96:4) to give the title compound. 1H-NMR (DMSO-d6) δ 1.58-1.69 (m, 1H), 1.91-2.01 (m, 1H), 2.20 (s, 6H), 3.19-3.27 (m, 1H), 3.28-3.36 (m, 1H), 3.88-3.97 (m, 1H), 4.05-4.19 (m, 2H), 4.48 (t, J=5.7 Hz, 1H), 4.56 (d, J=5.0 Hz, 1H), 6.94 (t, J=7.3 Hz, 1H), 7.05-7.14 (m, 3H), 7.27 (t, J=7.9 Hz, 2H), 7.85 (d, J=8.0 Hz, 2H), 8.08 (s, 1H), 8.36 (s, 1H), 9.65 (s, 1H). Mass Spectrum (ESI) m/e=419.2 (M+1).

Workup

  1. extractionextracted with CH2Cl2 (3×240 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customthe filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 96:4)

Sources & evidence

ORD record
ord-af78e56cf212483a91520c86a7e39e95
Source dataset
uspto-grants-2010_07
Patent number
US07763624B2

Reaction notes

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