tert-Butanol → HCID 86664794, compound

HRID 2369016Notes

Reaction equation

HRID 2369016 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]1[CH:13]=[N:14][N:15]3[C:20]([N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[CH:19][C:18]([CH:38]=C)=[N:17][C:16]=13)=[CH:5]2.CC([OH:44])(C)C.N1C(C)=CC=CC=1C.[O-]S([O-])(=S)=O.[Na+].[Na+]>O=[Os](=O)(=O)=O.O.C(Cl)Cl>[CH3:27][Si:26]([CH3:29])([CH3:28])[CH2:25][CH2:24][O:23][CH2:22][N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:36])[CH3:37])[C:20]1[N:15]2[N:14]=[CH:13][C:12]([C:6]3[CH:7]=[N:8][C:9]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[CH:11][CH:10]=4)=[C:16]2[N:17]=[C:18]([CH:38]=[O:44])[CH:19]=1

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 79372,6-LutidineHCID 24477Sodium ThiosulfateHCID 66584619HCID 66584619, compound

Product 1

HCID 86664794HCID 86664794, compoundYield 2,200%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To 3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5-vinylpyrazolo[1,5-a]pyrimidin-7-amine (1.3 g, 2.2 mmol) in 1,4-doixane (20 mL) was added 2.5 wt % OsO4 in t-BuOH (4.9 g, 0.1 mmol), 2,6-lutidine (1.1 mL, 9.0 mmol) and H2O (3 mL) and the resulting mixture was stirred at room temperature for 1 hour. NaIO4 (1.9 g, 8.9 mmol) was then added and stirring at room temperature was continued for 16 hours. LC/MS analysis at this time showed no starting material or diol intermediate present and confirmed full conversion to product. Saturated Na2S2O3 solution (30 mL) was added and the mixture stirred for 10 minutes. The reaction was transferred to a separatory funnel with CH2Cl2 (30 mL) and H2O (30 mL) and organics were extracted with CH2Cl2 (4×40 mL), dried (Na2SO4) and concentrated in vacuo to give 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidine-5-carbaldehyde as a brown solid (1.3 g, 2.2 mmol, 100%). LC/MS: 2.92 mins, m/z=568.3 (MH+).

Workup

  1. stirringstirring at room temperature
  2. waitwas continued for 16 hours
  3. stirringthe mixture stirred for 10 minutes
  4. extractionorganics were extracted with CH2Cl2 (4×40 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52931448df564e8d9872ed8afb8d68f2
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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