Dimethylformamide → HCID 59278335, compound

HRID 1698233Notes

Reaction equation

HRID 1698233 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:12])[C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.[CH3:13][N:14](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]([C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:12])[C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1)#[N:14]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 59278270HCID 59278270, compound

Product 1

HCID 59278335HCID 59278335, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

In a sealed tube was added N-(5-bromo-pyrimidin-2-yl)-N-methyl-acetamide (0.70 g, 3.04 mmol), Zn(CN)2 (0.59 g, 5.00 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.35 g, 0.30 mmol) in anhydrous DMF was degassed with Argon for 5 minutes and then warmed at 120° C. After 5 hours, the mixture was cooled and diluted with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 20% ethyl acetate in heptane. The major fractions were combined and the solvent was concentrated in vacuo to afford N-(5-cyano-pyrimidin-2-yl)-N-methyl-acetamide.

Workup

  1. customwas degassed with Argon for 5 minutes
  2. temperaturethe mixture was cooled
  3. additiondiluted with saturated aqueous NH4Cl
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 20% ethyl acetate in heptane
  10. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-c7a08bcd2baf4bce90a780a9c529a7f3
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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