tert-Butanol → 1-{4-Amino-1-[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}ethane-1,2-diol

HRID 1499844Notes

Reaction equation

HRID 1499844 reaction equation
[Br:1][C:2]1[C:3]([O:24][CH3:25])=[C:4]([CH:10]([N:12]2[C:16]3=[N:17][CH:18]=[N:19][C:20]([NH2:21])=[C:15]3C(C=C)=[N:13]2)[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].C[N+]1([O-])CC[O:30]CC1.[C:34]([OH:38])([CH3:37])([CH3:36])C>O.[Os](=O)(=O)(=O)=O>[NH2:21][C:20]1[N:19]=[CH:18][N:17]=[C:16]2[N:12]([CH:10]([C:4]3[CH:5]=[C:6]([Cl:9])[C:7]([CH3:8])=[C:2]([Br:1])[C:3]=3[O:24][CH3:25])[CH3:11])[N:13]=[C:36]([CH:34]([OH:38])[CH2:37][OH:30])[C:15]=12

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxide2×HCID 866777671-[1-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-3-vinyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 866777681-{4-Amino-1-[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}ethane-1,2-diol

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

To a solution of 1-[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-3-vinyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (100 mg, 0.236 mmol) in t-butyl alcohol (2 mL) was added N-methylmorpholine N-oxide (30.5 mg, 0.260 mmol) and water (0.74 mL). To the solution was then added aqueous osmium tetraoxide (0.075 mL, 4%). After 3 hr, another equivalent of N-methylmorpholine N-oxide was added. The reaction was stirred at room temperature overnight. The solution was diluted with water, extracted with ethyl acetate, dried over MgSO4 and concentrated to give the product which was used directly in the next step. LCMS calculated for C17H20BrClN5O3 (M+H)+: m/z=456.0; Found: 456.0

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto give the product which

Sources & evidence

ORD record
ord-9bb0a82910b0417a8e5b3f8a382b7d89
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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