n-Methyl-4-(trifluoromethoxy)aniline → N'-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-N-methyl-N-[4-(trifluoromethoxy)phenyl]urea

HRID 907415Notes

Reaction equation

HRID 907415 reaction equation
[N:1]([C:4]1[N:9]=[C:8]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[CH:7]=[C:6]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])[N:5]=1)=[C:2]=[O:3].[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1>C(Cl)Cl>[F:15][C:12]([F:13])([F:14])[CH2:11][O:10][C:8]1[CH:7]=[C:6]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])[N:5]=[C:4]([NH:1][C:2](=[O:3])[N:23]([CH3:22])[C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:26][CH:25]=2)[N:9]=1

Participants

4

Reactant 2

HCID 737351n-Methyl-4-(trifluoromethoxy)anilineHCID 576517972-Isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine

Product 1

HCID 57651686N'-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-N-methyl-N-[4-(trifluoromethoxy)phenyl]ureaYield 38.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine (400 mg, 1.26 mmol) in CH2Cl2 (1 mL) was added a solution of N-methyl-4-(trifluoromethoxy)aniline (285 mg, 1.50 mmol) in CH2Cl2 (2 mL). The resulting solution was stirred 18 h and then concentrated. The resulting residue was purified by column chromatography (silica, hexanes/EtOAc) to afford 7 as a white solid (247 mg, 38% yield): m.p. 100-102° C.; 1H NMR (CDCl3) δ 7.39 (app s, 4H), 5.96 (s, 1H), 6.82 (bs, 1H), 4.77-4.69 (q, 4H, J=8.5 Hz); ESI/MS 509 (M+H), 507 (M−H).

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was purified by column chromatography (silica, hexanes/EtOAc)

Sources & evidence

ORD record
ord-2945671dfde44ad39dd167745d4e00fb
Source dataset
uspto-grants-2011_09
Patent number
US08013154B2

Reaction notes

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