Potassium Carbonate → HCID 11625162, compound

HRID 732145Notes

Reaction equation

HRID 732145 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]3[CH2:12][CH2:13][CH2:14][NH:15][C:10]3=[N:9][N:8]=2)=[CH:3][CH:2]=1.Cl[CH2:17][C:18]1[O:22][C:21]([C:23]2[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=2)[C:26]#[N:27])=[N:20][N:19]=1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]3[CH2:12][CH2:13][CH2:14][N:15]([CH2:17][C:18]4[O:22][C:21]([C:23]5[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=5)[C:26]#[N:27])=[N:20][N:19]=4)[C:10]3=[N:9][N:8]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 201189383-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]benzonitrileHCID 1361179203-Pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine

Product 1

HCID 11625162HCID 11625162, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-pyridin-4-yl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrimidine (172 mg, 0.85 mmol) and 3-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]benzonitrile (94 mg, 0.43 mmol) were dissolved in butanone (5 ml) and K2CO3 (118 mg, 0.85 mmol) and KI (35 mg, 0.21 mmol) were added. The reaction mixture was refluxed for 1 h and the solvent was evaporated. The residue was dissolved in K2CO3 (aq., 1M, 25 ml) and was extracted with DCM. The combined organic layers were dried (Na2SO4) and purified with prep. HPLC to give the title compound (27 mg, 16%). 1H NMR: 8.75 (d, 2H), 8.30 (m, 2H), 7.79 (d, 1H), 7.63 (m, 1H), 7.53 (dd, 2H), 5.57 (d, 2H), 4.06 (t, 2H), 3.58 (t, 2H), 1.99 (m, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in K2CO3 (aq., 1M, 25 ml)
  4. extractionwas extracted with DCM
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. custompurified with prep

Sources & evidence

ORD record
ord-881f61bbebc54420bed2df1a8983e1ce
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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