Potassium Cyanide → 6-Cyano-pyrido[3,4-d]pyrimidin-4-one

HRID 566386Notes

Reaction equation

HRID 566386 reaction equation
Cl[C:2]1[N:12]=[CH:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[C-:13]#[N:14].[K+]>CN1CCCC1=O.[Cu]I>[C:13]([C:2]1[N:12]=[CH:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=[O:10])[C:4]=2[CH:3]=1)#[N:14]

Participants

5

Reactant 2

HCID 9032Potassium Cyanide2×HCID 1354805256-chloro-3H,4H-pyrido[3,4-d]pyrimidin-4-one

Product 1

HCID 1358174456-Cyano-pyrido[3,4-d]pyrimidin-4-oneYield 25.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

6-Chloro-pyrido[3,4-d]pyrimidin-4-one (10 g) in 1-methyl-2-pyrrolidinone (100 ml) was treated with copper (I) iodide (10.52 g) and potassium cyanide (7.10 g) at 215° C. for 72 hours under N2. Further potassium cyanide was added (3.58 g) and heating continued at 230° C. for 70 hours. The 1-methyl-2-pyrrolidinone was removed by distillation at reduced pressure and the residue absorbed onto silica. Chromatography gave the title compound (2.4 g) as a beige solid; δH [2H6]DMSO 13.0(1H, bs), 9.25 (1H,s), 8.55 (1H,s), 8.50 (1H,s); m/z (M+1+)171.

Workup

  1. temperatureheating
  2. customThe 1-methyl-2-pyrrolidinone was removed by distillation at reduced pressure
  3. customthe residue absorbed onto silica

Sources & evidence

ORD record
ord-ac777f4b78dd4acdbbaa5490568d3918
Source dataset
uspto-grants-2001_01
Patent number
US06174889B1

Reaction notes

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