Hydrochloric Acid → N*4*-(4-Bromo-phenyl)-6-(5-chloro-2-methoxy-phenyl)-pyrimidine-2,4-diamine

HRID 28533Notes

Reaction equation

HRID 28533 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[O:15][CH3:16])[N:5]=[C:4]([NH2:17])[N:3]=1.Cl.[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>C(O)C.O1CCOCC1>[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=3[O:15][CH3:16])[N:5]=[C:4]([NH2:17])[N:3]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 78074-BromoanilineHCID 860043134-Chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-2-yl-amine

Product 1

HCID 11350266N*4*-(4-Bromo-phenyl)-6-(5-chloro-2-methoxy-phenyl)-pyrimidine-2,4-diamineYield 98.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of 4-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-2-yl-amine (0.054 g, 0.20 mmol) in ethanol (7.5 ml) was added a solution of hydrogen chloride in dioxane (4.0 M, 0.025 ml) followed by 4-bromoaniline (0.069 g, 0.40 mmol). After heating under reflux for 45 minutes, volatiles were removed under reduced pressure. The residue was treated with 1.0 M hydrochloric acid (10 ml) and stirred for 30 minutes. Filtration provided the hydrochloride salt of the title compound (0.08 g, 90% yield). 1H NMR (DMSO-d6) δ 3.90 (s, 3H, CH3), 6.71 (s, 1H, Ar), 7.30 (d, 1H, J=9.0 Hz, Ar), 7.57-7.59 (m, 2H, Ar), 7.65 (dd, 1H, J=9.0 Hz, J=2.4 Hz, Ar), 7.70 (d, 1H, J=2.4 Hz, Ar), 7.80-7.86 (m, 2H, Ar), 11.08 (s, 1H, NH).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 45 minutes
  3. customvolatiles were removed under reduced pressure
  4. additionThe residue was treated with 1.0 M hydrochloric acid (10 ml)
  5. filtrationFiltration

Sources & evidence

ORD record
ord-03087b78bfff4b379f791079be59971a
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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