Ethylene Glycol → HCID 59570953, compound

HRID 2192931Notes

Reaction equation

HRID 2192931 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]([CH3:27])([CH3:26])[CH2:10][O:11][C:12]2[N:13]=[CH:14][C:15]([NH:18]C(=O)OC(C)(C)C)=[N:16][CH:17]=2)=[CH:5][CH:4]=1.O.NN.[OH-].[K+].C(O)CO>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([CH3:27])([CH3:26])[CH2:10][O:11][C:12]2[N:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 59571020HCID 59571020, compound

Product 1

HCID 59570953HCID 59570953, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of tert-butyl (5-{2-[(4-methoxybenzyl)oxy]-2-methylpropoxy}pyrazin-2-yl)carbamate (330 mg), hydrazine monohydrate (198 μL), potassium hydroxide (1.15 g), and ethylene glycol (9.9 mL) was stirred at 120° C. for 3 hours. To the reaction mixture was added water, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50) to obtain 5-{2-[(4-methoxybenzyl)oxy]-2-methylpropoxy}pyrazin-2-amine (220 mg) as a yellow oily substance.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50)

Sources & evidence

ORD record
ord-baacdb3bb8bb41478b6ad20c41abc29b
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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