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Allyl Alcohol → N,N-Dimethyl-3-[(prop-2-en-1-yl)oxy]pyrazin-2-amine

HRID 647961
Notes
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Reaction equation

HRID 647961 reaction equation
Cl[C:2]1[C:7]([N:8]([CH3:10])[CH3:9])=[N:6][CH:5]=[CH:4][N:3]=1.[CH2:11]([OH:14])[CH:12]=[CH2:13].[H-].[Na+]>CN(C)P(=O)(N(C)C)N(C)C>[CH2:11]([O:14][C:2]1[C:7]([N:8]([CH3:10])[CH3:9])=[N:6][CH:5]=[CH:4][N:3]=1)[CH:12]=[CH2:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydride2×HCID 204834273-Chloro-N,N-dimethylpyrazin-2-amine

Product 1

HCID 20483434N,N-Dimethyl-3-[(prop-2-en-1-yl)oxy]pyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
0 °C

Procedure

47 g of 2-chloro-3-dimethylamino-pyrazine and 35 g of allyl alcohol are dissolved in 300 ml of hexamethylphosphoric acid triamide. 14.4 g of sodium hydride are introduced into this solution at 0° C. over the course of 30 minutes. The mixture is then stirred for a further hour at 0° C. and for 15 hours at room temperature. The reaction mixture is then poured into 2 liters of ice water. After excess sodium hydride has been decomposed, the mixture is extracted by shaking with ether. The ether extracts are washed with water until neutral, dried over sodium sulphate and evaporated in a waterpump vacuum. The residue is distilled under reduced pressure. 2-Allyloxy-3-dimethylamino-pyrazine, boiling point 110°-115° C./10 mm Hg, is thus obtained.

Workup

  1. extractionthe mixture is extracted
  2. stirringby shaking with ether
  3. washThe ether extracts are washed with water until neutral,
  4. dry with materialdried over sodium sulphate
  5. customevaporated in a waterpump vacuum
  6. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-5e72ca776f00458b844b638db6e3a641
Source dataset
uspto-grants-1983_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04410530

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes