tert-Butanol → HCID 86677692, compound

HRID 1499761Notes

Reaction equation

HRID 1499761 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:13]([C:15]3[C:16]([O:34][CH2:35][CH3:36])=[C:17]([C:23]4[CH:24]=[CH:25][C:26]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[N:27][CH:28]=4)[C:18]([CH3:22])=[C:19]([Cl:21])[CH:20]=3)[CH3:14])[N:9]=C(C=C)[C:3]=12.C[N+]1([O-])CC[O:41]CC1.[C:45]([OH:49])([CH3:48])([CH3:47])C>O.[Os](=O)(=O)(=O)=O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:13]([C:15]3[C:16]([O:34][CH2:35][CH3:36])=[C:17]([C:23]4[CH:24]=[CH:25][C:26]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[N:27][CH:28]=4)[C:18]([CH3:22])=[C:19]([Cl:21])[CH:20]=3)[CH3:14])[N:9]=[C:47]([CH:45]([OH:49])[CH2:48][OH:41])[C:3]=12

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxide2×HCID 86677690HCID 86677690, compound

Product 1

HCID 86677692HCID 86677692, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

To a solution of 5-{3-[1-(4-amino-3-vinyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide (80 mg, 0.16 mmol, from Example 81, Step 1) in tert-butyl alcohol (1 mL) was added N-methylmorpholine N-oxide (20 mg, 0.17 mmol) and water (0.50 mL). To this solution was then added 4% osmium tetraoxide (5.0 μL, 0.00079 mmol). After stirring for 3 h, another equivalent of N-methylmorpholine N-oxide was added. The reaction was stirred at room temperature overnight. The solution was diluted with water, and extracted with EtOAc. The combined organic layers were dried over MgSO4 and filtered, concentrated to give the desired product (0.64 g, 95%). LCMS calculated for C26H31ClN7O4 (M+H)+: m/z=540.2; Found: 540.2.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1fc1e1bd10264fb3b4251361743e8b36
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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