Hydrochloric Acid → 5-bromo-N-(3-fluorophenyl)pyrimidin-2-amine

HRID 1404218Notes

Reaction equation

HRID 1404218 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[Br:9][C:10]1[CH:11]=[N:12][C:13](Cl)=[N:14][CH:15]=1.CCO.Cl>O>[Br:9][C:10]1[CH:11]=[N:12][C:13]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 97423-FluoroanilineHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 638743875-bromo-N-(3-fluorophenyl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In a microwave vial is added 3-fluorophenylamine (0.293 mL, 2.58 mmol), 5-bromo-2-chloropyrimidine (500 mg, 2.58 mmol), EtOH (10 mL) and concentrated HCl (0.2 mL). The reaction mixture is then heated at 50° C. for 15 min. Water (20 mL) is added and it is extracted with EtOAc. The organic layer is washed with NaHCO3, dried with Na2SO4 and concentrated. The residue is purified by column chromatography to give the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 6.83-6.88 (m, 1 H) 7.24-7.26 (m, 1 H) 7.28 (br. s., 1H) 7.34-7.40 (m, 1 H)7.74 (dt, J=11.37, 2.27 Hz, 1 H) 8.56 (s, 2 H); (M+H)+ 269.9.

Workup

  1. extractionit is extracted with EtOAc
  2. washThe organic layer is washed with NaHCO3
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-d6fdb9677a0744d4afe2d13b9b8d045b
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

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