5-Bromo-3-(3-trimethylsilanyl-prop-1-ynyl)-pyrazin-2-ylamine → 2-bromo-6-methyl-5H-pyrrolo[2,3-b]pyrazine

HRID 905986Notes

Reaction equation

HRID 905986 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:9]#[C:10][CH2:11][Si](C)(C)C)[C:5]([NH2:8])=[N:6][CH:7]=1.C(O[K])(C)(C)C>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[N:3]=[C:4]2[CH:9]=[C:10]([CH3:11])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 866423045-Bromo-3-(3-trimethylsilanyl-prop-1-ynyl)-pyrazin-2-ylamineHCID 178418922HCID 178418922, compound

Product 1

HCID 714334512-bromo-6-methyl-5H-pyrrolo[2,3-b]pyrazineYield 48.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-3-(3-trimethylsilanyl-prop-1-ynyl)-pyrazin-2-ylamine (1.66 g, 66% purity, 5.84 mmol) in 25 mL of THF was added a solution of tBuOK in THF (1M, 11.7 mL, 11.7 mmol) slowly at RT. The reaction mixture was heated to reflux for 2 days, then cooled to RT, diluted with EtOAc, quenched with H2O, filtered through a pad of celite, and washed with H2O and EtOAc. The organic layer was separated, washed with H2O and brine, dried (MgSO4), and concentrated to give 598 mg of 2-bromo-6-methyl-5H-pyrrolo[2,3-b]pyrazine as a brown solid (48% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 days
  3. customquenched with H2O
  4. filtrationfiltered through a pad of celite
  5. washwashed with H2O and EtOAc
  6. customThe organic layer was separated
  7. washwashed with H2O and brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-04727890f1a04a94b224ea04ba9ec2e5
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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