3,5-Dibromo-1-methyl-1H-pyrazin-2-one → HCID 86661229, compound

HRID 1918875Notes

Reaction equation

HRID 1918875 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([NH2:16])[CH:13]=[N:12]1)(C(C)(C)C)(C)C.Br[C:18]1[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=[C:22]([Br:24])[N:23]=1>CC(O)C>[Br:24][C:22]1[N:23]=[C:18]([NH:16][C:14]2[CH:13]=[N:12][N:11]([CH2:10][CH2:9][OH:8])[CH:15]=2)[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=1

Participants

4

Reactant 2

HCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-oneHCID 67016220HCID 67016220, compound

Product 1

HCID 86661229HCID 86661229, compoundYield 115.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A flask equipped with a magnetic stirrer was charged with 1-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-pyrazol-4-amine 116b (1.7 g, 7.1 mmol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (1.25 g, 4.7 mmol), and IPA (25 mL). The system was evacuated and then refilled with N2. The reaction mixture was heated at 90° C. for 6 h. Then, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash column chromatography eluting with petroleum ether/ethyl acetate to afford 140a (1.7 g, 78%). LCMS: [M+H]+ 314.

Workup

  1. customA flask equipped with a magnetic stirrer
  2. customThe system was evacuated
  3. additionrefilled with N2
  4. temperatureThen, the mixture was cooled to room temperature
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography
  7. washeluting with petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-0edd65f5a8b9415eb7ba9f0d4bb0b0a9
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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