Aminopyrazine → HCID 22046313, compound

HRID 1830712Notes

Reaction equation

HRID 1830712 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:12]=[C:13]=[O:14].[NH2:15][C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[NH:12][C:13]([NH:15][C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1)=[O:14]

Participants

4

Reactant 2

HCID 78747AminopyrazineHCID 34920221-isocyanato-2-methoxy-4-nitrobenzene

Product 1

HCID 22046313HCID 22046313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methoxy-4-nitrophenyl iso-cyanate (15.0 g, 77 mmol) and aminopyrazine (7.35 g, 77 mmol) in THF (600 mL) was stirred at reflux for 24 hours. The product precipitated from the cooled reaction mixture and was collected by filtration, washed with ethyl acetate, triturated with hot ethanol, and dried in vacuo (16.3 g, 73%). 1H NMR (300 Mhz, d6DMSO) δ: 10.50 (br s, 1H), 10.42 (s, 1H), 8.94 (s, 1H), 8.48 (d, 1H), 8.39 (s, 1H), 8.32 (d, 1H), 7.95 (dd, J=9.1, 2.4 Hz, 1H), 7.84(d, J=2.4 Hz, 1 H), 4.08 (s, 3H)

Workup

  1. temperatureat reflux for 24 hours
  2. customThe product precipitated from the cooled reaction mixture
  3. filtrationwas collected by filtration
  4. washwashed with ethyl acetate
  5. customtriturated with hot ethanol
  6. customdried in vacuo (16.3 g, 73%)

Sources & evidence

ORD record
ord-4d6c6ddcf9d64549b50eb2561f1fb0e1
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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