(3,5-diamino-6-chloropyrazin-2-yl)(1H-imidazol-1-yl)methanone → 6-chloropyrazine-2-carboxamide

HRID 1709997Notes

Reaction equation

HRID 1709997 reaction equation
N[C:2]1[C:3]([C:10]([N:12]2C=CN=C2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6](N)[N:7]=1>O1CCCC1>[Cl:9][C:5]1[N:4]=[C:3]([C:10]([NH2:12])=[O:11])[CH:2]=[N:7][CH:6]=1

Participants

3

Reactant 1

HCID 13020010(3,5-diamino-6-chloropyrazin-2-yl)(1H-imidazol-1-yl)methanone

Product 1

HCID 12825296-chloropyrazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

U.S. Pat. No. 3,201,472 as an example of how to obtain this material) in 700 ml of tetrahydrofuran was added 88.6 g (0.372 mol) of 1-(3,5-diamino-6-chloropyrazinoyl)imidazole (see U.S. Pat. No. 4,029,816 as an example of how to obtain this material) in 10 portions over 1.5 hours. After 1 hour at ambient temperature the reaction mixture was filtered and concentrated to 300 ml. The solution was added dropwise to 1.4 liters of ether with vigorous stirring. The solid was filtered, washed with ether and dried. There was obtained 74.3 g (0.258 mol, 70%) of 3,5-diamino-N-[2-(2-aminoethyl)methylamino]ethyl]-6-chloropyrazinecarboxamide. A sample was filtered through a pad of silica gel and eluted with 5:95 (v/v) methanol:methylene chloride saturated with ammonia gas; mp 138°-139.5° C.

Workup

  1. customover 1.5 hours
  2. filtrationAfter 1 hour at ambient temperature the reaction mixture was filtered
  3. concentrationconcentrated to 300 ml
  4. additionThe solution was added dropwise to 1.4 liters of ether with vigorous stirring
  5. filtrationThe solid was filtered
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-36671db3c8fb4a89850cf06063737b61
Source dataset
uspto-grants-1990_08
Patent number
US04952583

Reaction notes

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