Hydrochloric Acid → HCID 63874387, compound

HRID 76025Notes

Reaction equation

HRID 76025 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 63874387HCID 63874387, compound

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, 1H) 7.24-7.26 (m, 1H) 7.28 (br. s., 1H) 7.34-7.40 (m, 1H) 7.74 (dt, J=11.37, 2.27 Hz, 1H) 8.56 (s, 2H); (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-2f6d6c548ddf46d8a615ec91fcb055f1
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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