Ammonia → N-(4-(4-Aminopyrimidin-6-yl-oxy)phenyl)N'-(4chloro-3-trifluoromethyl-phenyl)-urea

HRID 1993517Notes

Reaction equation

HRID 1993517 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]([Cl:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH3:30]>C(O)C.O.CCOC(C)=O>[NH2:30][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]([Cl:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 58659336N-(4-(6-Chloropyrimidin-4yl-oxy)phenyl)-N'-(4-chloro-3-trifluoromethyl-phenyl)-urea

Product 1

HCID 58659396N-(4-(4-Aminopyrimidin-6-yl-oxy)phenyl)N'-(4chloro-3-trifluoromethyl-phenyl)-urea

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a sealed tube under N2-atmosphere, N-(4-(4-chloropyrimidin-6-yl-oxy)-phenyl)-N′-(4-chloro-3-trifluoromethyl-phenyl)-urea (443 mg, 1.00 mmol) and 25% aqueous NH3 (2 ml) in ethanol (2 ml) is stirred for 22 h at 80° C. Then the reaction mixture is diluted with water and AcOEt, the aqueous layer separated off and extracted 3 times with AcOEt. The organic phases are washed with 3 portions of water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; CH2Cl2/MeOH 9:1) yields the title compound: m.p.: 197-198° C.; 1H-NMR (DMSO6): 9.20 (s, HN), 8.93 (s, HN), 8.12 (m, 1H), 8.08 (s, 1H), 7.63 (m, 2H), 7.51 (d, 2H), 7.08 (d, 2H), 6.82 (s, H2N), 5.67 (s, 1H).

Workup

  1. customthe aqueous layer separated off
  2. extractionextracted 3 times with AcOEt
  3. washThe organic phases are washed with 3 portions of water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eb71248a3b8c4ba89498cb8b9d90f778
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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