Ethanol → HCID 118093612, compound

HRID 1520097Notes

Reaction equation

HRID 1520097 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][S:18]([NH:21][CH3:22])(=[O:20])=[O:19])=[CH:13][CH:12]=2)[CH:4]=1)#[N:2].CCO.CCOC(C)=O.[H][H]>[Pd].C(N(CC)CC)C>[NH2:2][CH2:1][C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][S:18]([NH:21][CH3:22])(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH:4]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 118093605HCID 118093605, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118093612HCID 118093612, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

In a PARR reactor, combine palladium (3.6 g, 10% on charcoal, 1-[4-(6-cyano-2-methyl-pyrimidin-4-yl)oxyphenyl]-N-methyl-methanesulfonamide (18 g, 56.5 mmol), EtOH (270 mL), EtOAc (270 mL), and triethylamine (31.5 mL). Seal the PARR reactor and charge it with hydrogen (400 psi); then shake the reactor at room temperature overnight. Open the reactor and filter the contents through CELITE®; wash the CELITE® pad with EtOH (1000 mL); collect the filtrate; and evaporate the solvent to provide the title compound as a brown solid (11.1 g, 43%). MS (m/z): 323 (M+1). Alternative Preparation 4

Workup

  1. customIn a PARR reactor, combine
  2. customSeal the PARR reactor
  3. customat room temperature
  4. customovernight
  5. filtrationfilter the contents through CELITE®
  6. washwash the CELITE® pad with EtOH (1000 mL)
  7. customcollect the filtrate
  8. customand evaporate the solvent

Sources & evidence

ORD record
ord-fac52defd7f840e3aced06d599061f03
Source dataset
uspto-grants-2015_07
Patent number
US09073901B2

Reaction notes

Loading…