Hydrochloric Acid → 2-Bromo-3-chloro-6-methyl-5H-pyrrolo[2,3-b]pyrazine

HRID 1521904Notes

Reaction equation

HRID 1521904 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:10]#[C:11][CH2:12][Si](C)(C)C)[C:5]([NH2:9])=[N:6][C:7]=1[Cl:8].CC([O-])(C)C.[K+].Cl>C(O)(C)(C)C.O>[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[C:11]([CH3:12])[NH:9][C:5]2=[N:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 866903235-Bromo-6-chloro-3-(3-(trimethylsilyl)prop-1-ynyl)pyrazin-2-amine

Product 1

HCID 866903242-Bromo-3-chloro-6-methyl-5H-pyrrolo[2,3-b]pyrazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

5-Bromo-6-chloro-3-(3-(trimethylsilyl)prop-1-ynyl)pyrazin-2-amine (step 2)(280 mg, 0.879 mmol) in tert-butanol (4 ml) at RT was treated with KOtBu (217 mg, 1.933 mmol) and heated at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with water and the pH adjusted to pH 1 using 2M HCl. The aqueous was extracted with DCM (×3) and the organic solvent removed under reduced pressure to afford the titled compound:

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous was extracted with DCM (×3)
  3. customthe organic solvent removed under reduced pressure

Sources & evidence

ORD record
ord-cff5061c3e004d3998b51b4dcbb83cf7
Source dataset
uspto-grants-2015_07
Patent number
US09073932B2

Reaction notes

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