Cyanide → HCID 53467828, compound

HRID 2401169Notes

Reaction equation

HRID 2401169 reaction equation
Br[C:2]1[C:3]([NH2:18])=[N:4][C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[N:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1.[C-:19]#[N:20].C(OCC)(=O)C>N1C=CC=CC=1>[NH2:18][C:3]1[C:2]([C:19]#[N:20])=[C:7]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[N:6]=[C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)[N:4]=1

Participants

5

Reactant 3

HCID 5975CyanideHCID 8857Ethyl AcetateHCID 534669585-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine

Product 1

HCID 53467828HCID 53467828, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.2 g (0.65 mmol) of 5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine and 0.06 g (0.72 mmol) of cupper (I) cyanide in 3 ml of pyridine was irradiated with microwaves at 250° C. for 20 min. After nearly complete conversion to the corresponding carbonitrile as was indicated by TLC, ethyl acetate was added and filtered throw celite. The solution was extracted two times with 10 ml of saturated solution of NaHCO3 and Brine. The organic layer was separated, dried with MgSO4 and concentrated to give 0.065 g (39.6%) of the desired product.

Workup

  1. customwas irradiated with microwaves at 250° C. for 20 min
  2. additionwas added
  3. filtrationfiltered
  4. extractionThe solution was extracted two times with 10 ml of saturated solution of NaHCO3 and Brine
  5. customThe organic layer was separated
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8b7352c0616d400a96ca13f3e0890d8c
Source dataset
uspto-grants-2014_08
Patent number
US08796284B2

Reaction notes

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