Methyl morpholine oxide → 4-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanol

HRID 334371Notes

Reaction equation

HRID 334371 reaction equation
C=C1C[CH2:6][CH:5]([C:8]2[CH:13]=[C:12]([N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:11]3[N:31]=[CH:32][CH:33]=[C:10]3[N:9]=2)[CH2:4]C1.C[N+]1([O-])CC[O:38][CH2:37]C1.[CH3:42][C:43]([CH3:45])=[O:44].O.CC#N>O=[Os](=O)(=O)=O>[CH3:21][Si:19]([CH3:20])([CH3:22])[CH2:18][CH2:17][O:16][CH2:15][N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:30])[CH3:29])[C:12]1[N:11]2[N:31]=[CH:32][CH:33]=[C:10]2[N:9]=[C:8]([CH:5]2[CH2:6][CH2:45][C:43]([CH2:37][OH:38])([OH:44])[CH2:42][CH2:4]2)[CH:13]=1

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 18799168Acetonitrile acetone waterHCID 665839235-(4-methylenecyclohexyl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 665839324-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanol

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a slurry of 5-(4-methylenecyclohexyl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (4.89 g, 10.0 mmol) in Acetone/H2O/MeCN (60/20/20) was added NMO (4.15 mL, 20 mmol), followed by OsO4 (2.5 wt. % in tBuOH) (6.27 mL, 0.50 mmol) at rt. The resulting reaction mixture was stirred at rt overnight. Organic solvent were evaporated and the aqueous residue was extracted with EtOAc three times, dried over Na2SO4 and concentrated to afford 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanol as a pale brownish oil (5.52 g), which was used without further purification. HPLC-MS TR=2.48 min (UV 254 nm, 5 min method); mass calculated for formula C25H46N4O4Si2 522.3, observed LCMS m/z 523.3 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. customOrganic solvent were evaporated
  3. extractionthe aqueous residue was extracted with EtOAc three times
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-64dd15f359ce432e85ac7ff9925b32a0
Source dataset
uspto-grants-2014_11
Patent number
US08883801B2

Reaction notes

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