Hexamethylenetetramine → 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

HRID 716050Notes

Reaction equation

HRID 716050 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C1N2CN3CN(C2)CN1C3.[C:21]([O-])([O-])=[O:22].[Na+].[Na+]>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([CH:21]=[O:22])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 10340Sodium CarbonateHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 575165872-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

To a reaction vial, 2-bromo-5H-pyrrolo[2,3-b]pyrazine (1 g, 0.00505 mol) was added in TFA (10 ml). Hexamine (1.06 g, 0.00757 mol) was added and reaction mixture was heated to 80° C. in microwave for 15 min. After completion of the reaction, the reaction mixture was poured into aq. Na2CO3 solution. Solid obtained was filtered, dried and purified using column purification by eluting with 3-5% EtOAc in Hexanes to yield 0.450 g of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde.

Workup

  1. customreaction mixture
  2. customAfter completion of the reaction
  3. customSolid obtained
  4. filtrationwas filtered
  5. customdried
  6. custompurified
  7. customcolumn purification
  8. washby eluting with 3-5% EtOAc in Hexanes

Sources & evidence

ORD record
ord-0f159efb45a846dabcd168ab551619d0
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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