Methanol → 2-Amino-3-cyano-5-methoxymethylpyrazine

HRID 279944Notes

Reaction equation

HRID 279944 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([CH2:10]Cl)=[CH:4][N:3]=1.[CH3:12][OH:13]>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([CH2:10][O:13][CH3:12])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 5837723-Amino-6-(chloromethyl)pyrazinecarbonitrile

Product 1

HCID 201641362-Amino-3-cyano-5-methoxymethylpyrazine

Procedure

2-Amino-3-cyano-5-chloromethyl pyrazine (0.95 g) was reacted with a large excess of dry methanol, under nitrogen, at reflux, for about 18 hours. The resulting reaction mixture was filtered and the filtrate was taken to dryness by evaporation. A yellow residue was collected and extracted twice with boiling methylene chloride. These extracts were filtered and the solvent evaporated to give 2-amino-3-cyano-5-methoxymethylpyrazine which was then treated with an excess of guanidine in methanol according to the method of Taylor (J. Org. Chem., 2817, 38, (1973)). Most of the product of this reaction precipitated and was collected by filtration. The filtrate was mixed with silica gel, stripped of solvent by evaporation, and the residue was placed on a silica gel column. This column was eluted with methanol (5%) in ethylacetate to yield a second crop of product which was added to that previously collected. The combined crops were recrystallized from methanol to yield 2,4-diamino-6-methoxymethyl pteridine (mp 248°-251°).

Workup

  1. temperatureunder nitrogen, at reflux, for about 18 hours
  2. customThe resulting reaction mixture
  3. filtrationwas filtered
  4. customthe filtrate was taken to dryness by evaporation
  5. customA yellow residue was collected
  6. extractionextracted twice with boiling methylene chloride
  7. filtrationThese extracts were filtered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-1c67e6017dbc469c9f43fa02af68260f
Source dataset
uspto-grants-1986_05
Patent number
US04587340

Reaction notes

Loading…