Pyridine → 1-[4-(6-Chloro-pyrimidin-4-yloxy)-phenyl]-3-p-tolyl-urea

HRID 1993533Notes

Reaction equation

HRID 1993533 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:3]=1.N1C=CC=CC=1.[C:22]1([CH3:31])[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1>CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:29]([NH:28][C:25]3[CH:26]=[CH:27][C:22]([CH3:31])=[CH:23][CH:24]=3)=[O:30])=[CH:11][CH:10]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 693254-Methylphenyl isocyanateHCID 226137114-((6-Chloropyrimidin-4-yl)oxy)aniline

Product 1

HCID 586593651-[4-(6-Chloro-pyrimidin-4-yloxy)-phenyl]-3-p-tolyl-urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(6-Chloro-pyrimidin-4-yloxy)-phenylamine (331 mg, 1.50 mmol) is dissolved in DMF (3 mL) under an argon atmosphere at rt. Pyridine (133.2 μL, 1.65 mmol) is added dropwise followed by dropwise addition of p-tolylisocyanate (221 μL, 1.80 mmol). The reaction Is stirred for 30 min at rt. The solvent is removed in vacuo and the residual crude product is titurated with ethyl acetate/hexanes 9:1 to give the title compound as a white powder: m.p.=217-219° C.; C18H15N4O2Cl: M+=355.1; 1H-NMR (DMSO-d6): 8.78 (s, 1H), 8.61 (s, 1H), 8.59 (s, 1H, HN), 7.52 (d, 2H), 7.37 (d, 2H), 7.17 (d, 2H), 7.05 (d, 2H), 2.21 (s, 3H).

Workup

  1. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e998a1ad2ca14e278a7ff945332a204b
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

Loading…