Pyrrolo[1,2-a]pyrazin-6-ylmethanol → Pyrrolo[1,2-a]pyrazine-6-carbaldehyde

HRID 2374141Notes

Reaction equation

HRID 2374141 reaction equation
[CH:1]1[C:2]2[N:3]([C:7]([CH2:10][OH:11])=[CH:8][CH:9]=2)[CH:4]=[CH:5][N:6]=1>CCOC(C)=O>[CH:1]1[C:2]2[N:3]([C:7]([CH:10]=[O:11])=[CH:8][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

3

Reactant 1

HCID 23356435Pyrrolo[1,2-a]pyrazin-6-ylmethanol

Product 1

HCID 23356469Pyrrolo[1,2-a]pyrazine-6-carbaldehydeYield 100.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Pyrrolo[1,2-a]pyrazin-6-yl-methanol (0.06 g, 0.41 mmol) is dissolved in EtOAc (3 mL), treated with IBX (0.34 g, 1.2 mmol) and heated to 80° C. for 3 h. The solution was allowed to cool to RT and filtered with a syringe filter frit. The solution was concentrated under a nitrogen stream to yield the title compound (0.06 g), which was used without further purification. 1H NMR (CDCl3) δ 9.87 (s, 1H), 9.34 (d, 1H), 9.02 (s, 1H), 7.93 (d, 1H), 7.47 (d, 1H), 6.82 (d, 1H).

Workup

  1. additiontreated with IBX (0.34 g, 1.2 mmol)
  2. temperatureto cool to RT
  3. filtrationfiltered with a syringe
  4. filtrationfilter frit
  5. concentrationThe solution was concentrated under a nitrogen stream

Sources & evidence

ORD record
ord-f611f6b5d6354bf082e4e971cb2a8c71
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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