Potassium tert-butoxide → HCID 86690311, compound

HRID 1428659Notes

Reaction equation

HRID 1428659 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[C:7]([NH2:26])=[N:8][C:9]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[N:11]=2)[CH2:3][CH2:2]1.CC(C)([O-])C.[K+]>C(O)(C)(C)C.O>[CH:1]1([C:4]2[NH:26][C:7]3=[N:8][C:9]([C:19]4[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=4)=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=4)[N:11]=[C:6]3[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86690310HCID 86690310, compound

Product 1

HCID 86690311HCID 86690311, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

3-(Cyclopropylethynyl)-5,6-di-p-tolylpyrazin-2-amine (step 4)(279 mg, 0.822 mmol) in tert-BuOH (10 ml) was treated with potassium tert-butoxide (184 mg, 1.644 mmol) and heated at reflux for 6 hours. The mixture was diluted with water and extracted with DCM (×3). The combined organic extracts were concentrated 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 as a beige coloured solid;

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. extractionextracted with DCM (×3)
  4. concentrationThe combined organic extracts were concentrated 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-6cbf3d3b1d5b485192215519cbd18cab
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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