Aminopyrazine → (2-Methoxy-5-nitrophenyl)-3-pyrazin-2-yl-urea

HRID 1830706Notes

Reaction equation

HRID 1830706 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[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>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[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 41675852-Methoxy-5-nitrophenyl isocyanate

Product 1

HCID 22046329(2-Methoxy-5-nitrophenyl)-3-pyrazin-2-yl-urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methoxy-5-nitrophenyl iso-cyanate (5.0 g, 25 mmol) and aminopyrazine (2.5 g, 26 mmol) in tetrahydrofuran (THF, 250 mL) was stirred at reflux for 24 hours. The product was precipitated from the cooled reaction mixture and was collected by filtration, washed with ethyl acetate, and dried in vacuo (4.3 g, 57%). 1H NMR (300 MHz, d6-DMSO) (mixture of rotamers) δ: 10.38 (br, s, 1H), 10.27 (s, 1H), 9.39, 8.88 (2 singlets, 1H), 9.10(d, 1H), 8.33 (s, 1H), 8.26 (d, 1H), 7.98-8.25 (m, 1H), 7.97-7.84 (m, 1H), 4.05, 4.03 (2 singlets, 77:28 ratio, 3H).

Workup

  1. temperatureat reflux for 24 hours
  2. customThe product was precipitated from the cooled reaction mixture
  3. filtrationwas collected by filtration
  4. washwashed with ethyl acetate
  5. customdried in vacuo (4.3 g, 57%)

Sources & evidence

ORD record
ord-6f7ea9b0c6bb4575a553f1d5053a3aaa
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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