Methanol → HCID 11395628, compound

HRID 28553Notes

Reaction equation

HRID 28553 reaction equation
Cl[C:2]1[N: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])[CH:3]=1.[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.CO.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:2]2[CH:3]=[C:4]([NH2:17])[N:5]=[C:6]([C:8]3[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=3[O:15][CH3:16])[N:7]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 78074-BromoanilineHCID 10340Sodium CarbonateHCID 865946016-Chloro-2-(5-chloro-2-methoxy-phenyl)-pyrimidin-4-yl-amine

Product 1

HCID 11395628HCID 11395628, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of the hydrochloride salt of 6-chloro-2-(5-chloro-2-methoxy-phenyl)-pyrimidin-4-yl-amine (0.020 g, 0.065 mmol) in ethanol (5.0 ml) was added 4-bromoaniline (0.022 g, 0.13 mmol). After heating under reflux for 20 hours, the solvent was evaporated under reduced pressure. The residue was treated with 1.0 M hydrochloric acid (10 ml) and stirred for 30 minutes. Filtration provided a solid which was treated with methanol (10 ml) and stirred while a solution of sodium carbonate in water (1.0 M, 1 ml) was added. After stirring for 1 hour, the solvents were evaporated under reduced pressure. The residue was treated with water (10 ml) and stirred for 15 minutes. Filtration provided the title compound (0.011 g, 42% yield) as a beige powder. 1H NMR (DMSO-d6) δ 3.83 (s, 3H, CH3), 5.74 (s, 1H, Ar), 6.50 (s, 2H, NH2), 7.14 (d, 1H, J=8.9 Hz, Ar), 7.40-7.45 (m, 3H, Ar), 7.55 (d, 1H, J=2.7 Hz), 7.65-7.67 (m, 2H, Ar), 9.16 (s, 1H, NH).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 20 hours
  3. customthe solvent was evaporated under reduced pressure
  4. additionThe residue was treated with 1.0 M hydrochloric acid (10 ml)
  5. filtrationFiltration
  6. customprovided a solid which
  7. additionwas added
  8. stirringAfter stirring for 1 hour
  9. customthe solvents were evaporated under reduced pressure
  10. additionThe residue was treated with water (10 ml)
  11. stirringstirred for 15 minutes
  12. filtrationFiltration

Sources & evidence

ORD record
ord-4ad5e7f168374afdae6badcec0fb3220
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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