2-Aminopyrimidine → HCID 15754624, compound

HRID 416661Notes

Reaction equation

HRID 416661 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=O.[NH2:14][C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1>CC(C)=O>[N+:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]1[N:14]=[C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]2[CH:2]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 2440252-Bromo-2'-nitroacetophenone

Product 1

HCID 15754624HCID 15754624, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Bromo-2′-nitroacetophenone (5.0 g, 20.4 mmol) and 2-aminopyrimidine (1.94 g, 20.4 mmol) were dissolved in acetone (50 ml) and brought to reflux. After 60 minutes a light white precipitate developed. Refluxing was continued for 5.5 hours and cooled to room temperature. The volume was reduced ½ by evaporation and the intermediate solids were collected by filtration, washed with acetone (20 ml) and air dried (2.84 g of intermediate). A second crop was collected by concentration of the combined mother liquors, and refluxing the residue in fresh acetone (20 ml) for 1.5 hours. Upon cooling, and reducing the volume by ½ by evaporation, 3.11 g of solids were collected. The combined solid intermediate (5.95 g) was dissolved in MeOH (70 ml) with 5 drops of conc. HBr and refluxed for 2 hours. After cooling the volume was reduced by ½, water (40 ml) was added solution was made basic (pH=10) with 1N NaOH. Roto-evaporation to remove methanol resulted in the product crystallizing. The product was filtered, washed with water and air dried to obtain 5.03 g of the desired product. (MS, M++H=241.0)

Workup

  1. temperatureto reflux
  2. temperatureRefluxing
  3. waitwas continued for 5.5 hours
  4. customby evaporation
  5. filtrationthe intermediate solids were collected by filtration
  6. washwashed with acetone (20 ml) and air
  7. dry with materialdried (2.84 g of intermediate)
  8. customA second crop was collected by concentration of the combined mother liquors
  9. temperaturerefluxing the residue in fresh acetone (20 ml) for 1.5 hours
  10. temperatureUpon cooling
  11. customby evaporation, 3.11 g of solids
  12. customwere collected
  13. dissolutionThe combined solid intermediate (5.95 g) was dissolved in MeOH (70 ml) with 5 drops of conc. HBr
  14. temperaturerefluxed for 2 hours
  15. temperatureAfter cooling the volume
  16. additionwas added solution
  17. customRoto-evaporation
  18. customto remove methanol
  19. customresulted in the product
  20. customcrystallizing
  21. filtrationThe product was filtered
  22. washwashed with water and air
  23. customdried

Sources & evidence

ORD record
ord-0765137d5b3b4ad68a38f28e73797fd2
Source dataset
uspto-grants-2012_01
Patent number
US08088928B2

Reaction notes

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