Tetrahydrofuran → (3-Amino-pyrazin-2-YL)-phenyl-methanone

HRID 1075769Notes

Reaction equation

HRID 1075769 reaction equation
[NH2:1][C:2]1[C:7]([C:8](N2CCCC2)=[O:9])=[N:6][CH:5]=[CH:4][N:3]=1.[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O1CCCC1>O>[NH2:1][C:2]1[C:7]([C:8](=[O:9])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 539368772-Aminopyrazine-3-carboxylic acid pyrrolidideHCID 178418255HCID 178418255, compound

Product 1

HCID 10899618(3-Amino-pyrazin-2-YL)-phenyl-methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Aminopyrazine-3-carboxylic acid pyrrolidide (63.4 g. or 0.33 mol) was added to a solution of freshly prepared phenylmagnesium bromide (305 g.) in 1 l. of tetrahydrofuran while the temperature was kept at 20°-30° by cooling with an ice bath. After stirring at room temperature for 2 hours, the mixture was hydrolyzed by addition of 2 l. of water. The aqueous layer was extracted twice with 500 ml. of methylene chloride. The extracts were combined with the organic layer, dried over sodium sulfate and evaporated. The brown residue was slurried with ether to yield 37.5 g. (56%) of yellow crystals of the above-named product.

Workup

  1. customwas kept at 20°-30°
  2. temperatureby cooling with an ice bath
  3. additionthe mixture was hydrolyzed by addition of 2 l
  4. extractionThe aqueous layer was extracted twice with 500 ml
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto yield 37.5 g

Sources & evidence

ORD record
ord-b02e473201f7415486d64d8269502233
Source dataset
uspto-grants-1976_05
Patent number
US03954753

Reaction notes

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