Hydrochloric Acid → HCID 86690338, compound

HRID 1428690Notes

Reaction equation

HRID 1428690 reaction equation
[C:1]1([CH3:27])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]([C:21]#[C:22][Si](C)(C)C)[C:10]([NH2:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Cl.[OH-].[Na+]>C(O)(C)(C)C.O>[C:1]1([CH3:27])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH:21]=[CH:22][NH:20][C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23665647Potassium tert-butoxideHCID 86690339HCID 86690339, compound

Product 1

HCID 86690338HCID 86690338, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

5,6-Di-p-tolyl-3-((trimethylsilyl)ethynyl)pyrazin-2-amine (step 4) (170 mg, 0.458 mmol) in tert-BuOH (5 ml) at RT was treated with potassium tert-butoxide (205 mg, 1.830 mmol) and heated at reflux for 3 hours. After cooling to RT, conc. HCl (0.5 ml, 16.46 mmol) was added and the mixture was heated at reflux for 3 hours and stirred at RT overnight. The mixture was added to water (100 ml) and the pH was adjusted to pH 10 using 2M NaOH. The aqueous portion was extracted with DCM (×3) and the combined organic extracts were passed through a phase separating column. The solvent was removed under reduced pressure and purification of the crude product by chromatography on silica eluting with 0-20% EtOAc in iso-hexane afforded the titled compound;

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 3 hours
  5. extractionThe aqueous portion was extracted with DCM (×3)
  6. customseparating column
  7. customThe solvent was removed under reduced pressure and purification of the crude product by chromatography on silica eluting with 0-20% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-09e170d7050f414b877ea3b36845a353
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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