Methanol → HCID 118093616, compound

HRID 1520101Notes

Reaction equation

HRID 1520101 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]([N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:20])=[O:19])=[CH:13][CH:12]=2)[CH:4]=1)#[N:2].C(N(CC)CC)C.CO.[H][H]>[Pd].C1(C)C=CC=CC=1.CCOC(C)=O>[NH2:2][CH2:1][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]([N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])(=[O:20])=[O:19])=[CH:13][CH:12]=2)[CH:4]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 118093617HCID 118093617, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 118093616HCID 118093616, compoundYield 140.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine tert-butyl N-[[4-(6-cyano-2-methyl-pyrimidin-4-y)oxyphenyl]methylsulfonyl]-N-methyl-carbamate (400 mg, 0.96 mmol), triethylamine (290 mg, 2.9 mmol), MeOH (20 mL), and EtOAc (20 mL) in a PARR reactor. Add 5% palladium on carbon (203 mg, 0.096 mmol). Seal the PARR reactor and pressurize it with hydrogen (345 kPa). Shake the reactor at ambient temperature for 17 hours. Depressurize and open the reactor. Add an additional amount of 5% palladium on carbon (200 mg, 0.094 mmol); re-pressurize the reactor with hydrogen (414 kPa) and shake the reactor for an addition 17 hours while maintaining it at ambient temperature. Depressurize and open the reactor. Filter the contents through diatomaceous earth, and concentrate the filtrate under reduced pressure to provide a residue. To purify, add toluene and concentrate under reduced pressure to provide an orange-red residue. Repeat the toluene addition and removal 3 times to provide the title compound as a pink solid (0.57 g, 98.8%, 70% pure). MS (m/z): 423 (M+1).

Workup

  1. customSeal the PARR reactor
  2. additionfor an addition 17 hours
  3. filtrationFilter the contents through diatomaceous earth
  4. concentrationconcentrate the filtrate under reduced pressure
  5. customto provide a residue
  6. customTo purify
  7. additionadd toluene
  8. concentrationconcentrate under reduced pressure
  9. customto provide an orange-red residue

Sources & evidence

ORD record
ord-ca3385a8f644418e95dddce9bd0db210
Source dataset
uspto-grants-2015_07
Patent number
US09073901B2

Reaction notes

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