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

HRID 1701737
Notes
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Reaction equation

HRID 1701737 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-79c6620ebedc410ebd17c14cfa87d02b
Source dataset
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04195090

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes