Dimethylformamide → HCID 118093605, compound

HRID 1520096Notes

Reaction equation

HRID 1520096 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][S:17]([NH:20][CH3:21])(=[O:19])=[O:18])=[CH:12][CH:11]=2)[CH:3]=1.[CH3:22][N:23](C=O)C>O.[C-]#N.[Zn+2].[C-]#N>[C:22]([C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][S:17]([NH:20][CH3:21])(=[O:19])=[O:18])=[CH:12][CH:11]=2)[CH:3]=1)#[N:23]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 118093609HCID 118093609, compound

Product 1

HCID 118093605HCID 118093605, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Bubble nitrogen gas through a solution of 1-[4-(6-chloro-2-methyl-pyrimidin-4-yl)oxyphenyl]-N-methyl-methanesulfonamide (26.6, 81.1 mmol) in DMF (266.0 mL) for 15 minutes. Thereafter add zinc cyanide (14.59 g, 121.2 mmol) and (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) chloride (6.76 g, 8.1 mmol). Heat the suspension to 150° C. for 6 hr while maintaining it under a nitrogen atmosphere. Cool the mixture to room temperature. Dilute the mixture with water (600 mL) and extract the mixture with EtOAc (3×500 mL). Combine the EtOAc extracts. Sequentially wash the combined extracts with water (500 mL) then brine (500 mL); dry over sodium sulfate; filter and concentrate the filtrate under reduced pressure. Isolate the title compound using silica gel chromatography eluting with hexane/EtOAc (1:1) to give the title compound (18 g, 70%). MS (m/z): 319 (M+1).

Workup

  1. temperaturewhile maintaining it under a nitrogen atmosphere
  2. temperatureCool the mixture to room temperature
  3. extractionextract the mixture with EtOAc (3×500 mL)
  4. washSequentially wash the combined extracts with water (500 mL)
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-5b558d6264e24aa388453713a2713e32
Source dataset
uspto-grants-2015_07
Patent number
US09073901B2

Reaction notes

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