Pyrrolidine → 2-Aminopyrazine-3-carboxylic acid pyrrolidide

HRID 1075767Notes

Reaction equation

HRID 1075767 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10]C)=O)=[N:6][CH:5]=[CH:4][N:3]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>CO>[NH2:1][C:2]1[C:7]([C:8]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:10])=[N:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 72669Methyl 3-aminopyrazinecarboxylate

Product 1

HCID 539368772-Aminopyrazine-3-carboxylic acid pyrrolidide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 10 g. (0.065 mol) of methyl 2-aminopyrazine-3-carboxylate in 100 ml. of methanol and 25 ml. of pyrrolidine was refluxed for 18 hours. The residue obtained after evaporation under reduced pressure was triturated with ether to yield 8.8 g. (70%) of the above-named product as yellow crystals, with m.p. 100°-105°. A second crop of 2.3 g. (18%) with m.p. 95°-105° was obtained from the mother liquors. The analytical sample was recrystallized from 2-propanol. The pale yellow prisms had a melting point of 104°-106°.

Workup

  1. customThe residue obtained
  2. customafter evaporation under reduced pressure
  3. customwas triturated with ether
  4. customto yield 8.8 g
  5. custom(18%) with m.p. 95°-105° was obtained from the mother liquors
  6. customThe analytical sample was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-67a7a9ff92cf4ffa887a17b8c8ce24d9
Source dataset
uspto-grants-1976_05
Patent number
US03954753

Reaction notes

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