2-Isocyanato-1-methoxy-4-methylbenzene → 3-(2-Methoxy-5-methyl-phenyl)-1-methyl-1-pyrazin-2-yl-urea

HRID 1830757Notes

Reaction equation

HRID 1830757 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[N:18]=[C:19]=[O:20].CCOC(C)=O.CCCCCC.C(Cl)Cl.CO>ClC(Cl)C>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[NH:18][C:19](=[O:20])[N:2]([CH3:1])[C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 41415202-Isocyanato-1-methoxy-4-methylbenzeneHCID 16767478N-Methylpyrazin-2-amineHCID 21226129Dichloromethane methanolHCID 21226206Ethyl acetate hexane

Product 1

HCID 220464313-(2-Methoxy-5-methyl-phenyl)-1-methyl-1-pyrazin-2-yl-urea

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 0.3 M stirred solution of 2-methylaminopyrazine (1 equiv.) in dichloroethane at room temperature under nitrogen was added 2-methoxy-5-methylphenylisocyanate (1 equiv.). The reaction was warmed to 80° C. overnight and then cooled to room temperature. In most cases, the product precipitated and was isolated by filtration. Alternatively the product could be isolated by silica gel chromatography using EtOAc/hexane or CH2Cl2/MeOH as eluant. 1H-NMR (400 MHz, CDCl3) δ8.57 (s, 1H), 8.32 (s, 1H), 8.31 (s, 1H), 8.17 (s, 1H), 6.80 (i, 2H), 3.90 (s, 3H), 3.56 (s, 3H), 2.32 (s, 3H). LRMS (ESI, Positive) m/e 273.2 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. customIn most cases, the product precipitated
  3. customwas isolated by filtration
  4. customAlternatively the product could be isolated by silica gel chromatography

Sources & evidence

ORD record
ord-7757c99411094b4eafe7b8902b065176
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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