Bromine → HCID 178508940, compound

HRID 1647707Notes

Reaction equation

HRID 1647707 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[N:3]=1.[Br:16]Br>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([Br:16])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178508964HCID 178508964, compound

Product 1

HCID 178508940HCID 178508940, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To 3.13 g. (15 mM) of 2-amino-6-(m-chlorophenyl)-4-pyrimidinol is added 80 ml. of glacial acetic acid. The solution is heated to 80° C. and 0.81 ml. of Br2 is added. The mixture is allowed to stir at 80° C. for 15 minutes and cooled to 2.5° C. The mixture is evaporated to dryness under vacuum at 40° C. and the resulting solids heated at reflux with 150 ml. of water. The reaction mixture is cooled and filtered, and the solids washed very well with cold water. The solids are dried at 60° C. in a vacuum oven and pulverized when dry. The boiling water tritration is repeated. 3.90 G. (86.9%) of title compound is recovered. Recrystallization of the solids from water:DMF by adding DMF slowly to a stirring slurry of 3.9 g. of compound in 150 ml. boiling water until solution occurs, cooling and filtering yields analytically pure material (80% recovery).

Workup

  1. temperaturecooled to 2.5° C
  2. customThe mixture is evaporated to dryness under vacuum at 40° C.
  3. temperaturethe resulting solids heated
  4. temperatureat reflux with 150 ml
  5. temperatureThe reaction mixture is cooled
  6. filtrationfiltered
  7. washthe solids washed very well with cold water
  8. customThe solids are dried at 60° C. in a vacuum oven
  9. customdry
  10. custom(86.9%) of title compound is recovered
  11. customRecrystallization of the solids from water
  12. additionDMF by adding DMF slowly to a stirring slurry of 3.9 g
  13. temperaturecooling
  14. filtrationfiltering
  15. customyields analytically pure material (80% recovery)

Sources & evidence

ORD record
ord-75af2acd17f2498880ad57dd5799a512
Source dataset
uspto-grants-1995_07
Patent number
US05434157

Reaction notes

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