Benzenamine, 4-(4-morpholinyl)- → 5-Bromo-1-methyl-3-(4-morpholinophenylamino)pyrazin-2(1H)-one

HRID 1918842Notes

Reaction equation

HRID 1918842 reaction equation
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[N:7]=1.[O:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1>C(O)(C)C>[Br:8][C:6]1[N:7]=[C:2]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([N:14]3[CH2:15][CH2:16][O:11][CH2:12][CH2:13]3)=[CH:22][CH:21]=2)[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=1

Participants

4

Reactant 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-one

Product 1

HCID 666134025-Bromo-1-methyl-3-(4-morpholinophenylamino)pyrazin-2(1H)-oneYield 85.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A microwave vial equipped with a magnetic stirrer was charged with 3,5-dibromo-1-methylpyrazin-2(1H)-one (1.97 g, 7.4 mmol), 4-morpholinobenzenamine (1.97 g, 11.1 mmol), and isopropanol (25 mL). The system was evacuated and then refilled with N2. It was heated at 90° C. for 16 h. Then, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash column chromatography eluting with 5:1 petroleum ether/ethyl acetate to afford 122a (2.3 g, 85%). LCMS: [M+H]+ 365.

Workup

  1. customA microwave vial 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 5:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-843d8691b3f040e58fc00f5e5474e91e
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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