Methylamine ethanol → HCID 58659378, compound

HRID 1993515Notes

Reaction equation

HRID 1993515 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:29][NH2:30].C(O)C>>[CH3:29][NH:30][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:26])([CH3:28])[CH3:27])=[CH:21][CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 22028356Methylamine ethanolHCID 58659380HCID 58659380, compound

Product 1

HCID 58659378HCID 58659378, compound

Procedure

Under N2-atmosphere, a solution of N-(4-(4-chloropyrimidin-6-yl-oxy)-phenyl)-N′-(4-tert-butylphenyl)-urea (319 mg, 0.80 mmol) in methylamine/ethanol (8.03 M; 5 ml) is stirred for 50 min at 40° C. Then the reaction mixture is concentrated in vacuo, the residue re-dissolved in water and AcOEt, the aqueous layer separated off and extracted twice with AcOEt. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated in vacuo after adding 2 g of SiO2. The resulting powder is put on top of a SiO2-column and eluted with AcOEt/hexane 9:1, yielding the title compound: m.p.: 245-246° C.; 1H-NMR (DMSO-d6): 8.7 (s, HN), 8.6 (s, HN), 8.13 (s, 1H), 7.45 (d, 2H), 7.35 (d, 2H), 7.31 (d, 2H), 7.05 (d, 2H), 6.78 (s, HN), 5.79 (s, 1H), 2.83 (MeN), 1.30 (Me3C).

Workup

  1. concentrationThen the reaction mixture is concentrated in vacuo
  2. dissolutionthe residue re-dissolved in water
  3. customAcOEt, the aqueous layer separated off
  4. extractionextracted twice with AcOEt
  5. washThe organic phases are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. additionafter adding 2 g of SiO2
  9. washeluted with AcOEt/hexane 9:1

Sources & evidence

ORD record
ord-f7122ee4b556491eadc89674fc35cdd0
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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