Potassium Carbonate → 3-{3-[(3-pyridin-4-yl-6,7-dihydro[1,2,4]triazolo[4,3-a]pyrimidin-8(5H)-yl)methyl]-1,2,4-oxadiazol-5-yl}benzonitrile

HRID 732146Notes

Reaction equation

HRID 732146 reaction equation
CS(O[CH2:6][C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)[O:9][N:8]=1)(=O)=O.[N:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:30]3[CH2:31][CH2:32][CH2:33][NH:34][C:29]3=[N:28][N:27]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[N:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:30]3[CH2:31][CH2:32][CH2:33][N:34]([CH2:6][C:7]4[N:11]=[C:10]([C:12]5[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=5)[C:18]#[N:19])[O:9][N:8]=4)[C:29]3=[N:28][N:27]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57837975[5-(3-Cyanophenyl)-1,2,4-oxadiazol-3-yl]methyl methanesulfonateHCID 1361179203-Pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine

Product 1

HCID 115092473-{3-[(3-pyridin-4-yl-6,7-dihydro[1,2,4]triazolo[4,3-a]pyrimidin-8(5H)-yl)methyl]-1,2,4-oxadiazol-5-yl}benzonitrileYield 1.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

[5-(3-cyanophenyl)-1,2,4-oxadiazol-3-yl]methyl methanesulfonate (0.278 g; 0.99 mmol) and 3-pyridin-4-yl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrimidine (0.220 g; 1.09 mmol) were dissolved in butanone (20 ml) and potassium carbonate (0.275 g; 1.99 mmol) was added portionwise. The mixture was heated at reflux for 18 h before cooling to r.t. This mixture was concentrated in vacuo and DCM (20 ml) was added. The mixture was washed with water, dried (Na2SO4), evaporated and purified using prep. HPLC chromatography to give the title compound (5.4 mg). 1H NMR: 8.77 (m, 2H), 8.41 (s, 1H), 8.34 (d, 1H), 7.87 (d, 1H), 7.68 (t, 1H), 7.56 (m, 2H) 5.51 (s, 2H), 4.09 (m, 2H), 3.62 (m, 2H), 2.19 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationThis mixture was concentrated in vacuo and DCM (20 ml)
  4. additionwas added
  5. washThe mixture was washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. custompurified

Sources & evidence

ORD record
ord-fe98b22049d64d00bf8ddcdf77658498
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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