Methanol → 5-(Hydroxymethyl)pyrazine-2-carboxamide

HRID 1373151Notes

Reaction equation

HRID 1373151 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([NH2:9])=[O:8].[OH2:10].S(=O)(=O)(O)O.NOS(O)(=O)=O.[CH3:22]O>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[OH:10][CH2:22][C:5]1[N:4]=[CH:3][C:2]([C:7]([NH2:9])=[O:8])=[N:1][CH:6]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 962WaterHCID 1046PyrazinamideHCID 1118Sulfuric Acid2×HCID 76284hydroxylamine-O-sulfonic acid

Product 1

HCID 378192135-(Hydroxymethyl)pyrazine-2-carboxamideYield 17%

Reagents, catalysts & solvents 1

HCID 62662Ferrous sulfate heptahydrateCatalyst2×

Procedure

Pyrazinecarboxylic acid amide (0.492 g, 4 mmol) was suspended in methanol (8 ml), water (4 ml) and concentrated sulphuric acid (0.22 ml, 4 mmol), then iron (II) sulphate heptahydrate (0.334 g, 1.2 mmol) was added and the mixture degassed. To this was then added hydroxylamine-O-sulphonic acid (1.36 g, 12 mmol). After 6 h more sulphuric acid and iron (II) sulphate heptahydrate were added. After a further 1 h the mixture was adjusted to pH 7, evaporated, and the residue extracted with methanol. This solution was pre-absorbed onto silica then purified by chromatography, eluting with 0–10% ‘2 M ammonia in methanol’ in dichloromethane, to give the title compound as an off-white solid (0.102 g, 17%); NMR [(CD3)2SO] 4.72 (2H, d), 5.72 (1H, t), 7.79 (1H, br s), 8.22 (1H, br s), 8.73 (1H, d), and 9.09 (1H, d).

Workup

  1. customthe mixture degassed
  2. customevaporated
  3. extractionthe residue extracted with methanol
  4. customThis solution was pre-absorbed onto silica
  5. customthen purified by chromatography
  6. washeluting with 0–10% ‘2 M ammonia in methanol’ in dichloromethane

Sources & evidence

ORD record
ord-0c35811c347840c5b06821d7c2c4f8c0
Source dataset
uspto-grants-2007_01
Patent number
US07160907B2

Reaction notes

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