Benzyl Bromide → HCID 178481262, compound

HRID 979103Notes

Reaction equation

HRID 979103 reaction equation
[CH2:1]([N:8]1[C:13]2=[N:14][C:15]3[N:16]([CH3:23])[CH2:17][N:18]([CH3:22])[C:19](=[O:21])[C:20]=3[N:12]2[C:11]([OH:24])=[CH:10][C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CC(C)=O>[CH2:33]([C:10]1[C:9](=[O:25])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13]2[N:12]([C:11]=1[OH:24])[C:20]1[C:19](=[O:21])[N:18]([CH3:22])[CH2:17][N:16]([CH3:23])[C:15]=1[N:14]=2)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 178481263HCID 178481263, compound

Product 1

HCID 178481262HCID 178481262, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 7.1 g. (0.021 mole) of 9-benzyl-2,3-dihydro-1,3-dimethyl-6-(hydroxy)pyrimido[2,1-f]purine-4,8(1H,9H)-dione in 200 ml. of acetone, add 2.3 g. (0.023 mole) of triethylamine, and stir the mixture for 5 minutes at room temperature under a nitrogen atmosphere to obtain a clear solution. Add dropwise to the solution 4.7 g. (0.027 mole) of benzyl bromide, and reflux the mixture for 5 hours under a nitrogen atmosphere. Remove the acetone under reduced pressure, and triturate the gummy residue with methanol. Remove the resultant white solid by filtration, pour the filtrate into water, acidify to pH 4-5 with dilute hydrochloric acid, and decant the aqueous supernatant. Dissolve the gummy residue in the chloroform, wash the solution with water, and dry over anhydrous magnesium sulfate. Remove the drying agent by filtration, and evaporate solvent from the filtrate under reduced pressure. Chromatograph the residual oil on silica gel, eluting with chloroform(96)-methanol(4), to obtain the title compound as a solid with m.p. 176°-179° C.

Workup

  1. additionTo a suspension of 7.1 g
  2. customto obtain a clear solution
  3. customRemove the acetone under reduced pressure
  4. customtriturate the gummy residue with methanol
  5. customRemove the resultant white solid
  6. filtrationby filtration
  7. additionpour the filtrate into water
  8. customdecant the aqueous supernatant
  9. dissolutionDissolve the gummy residue in the chloroform
  10. washwash the solution with water
  11. dry with materialdry over anhydrous magnesium sulfate
  12. customRemove the drying agent
  13. filtrationby filtration
  14. customevaporate solvent from the filtrate under reduced pressure
  15. washChromatograph the residual oil on silica gel, eluting with chloroform(96)-methanol(4)

Sources & evidence

ORD record
ord-aafc99bb55a749d58e9baedc3465dee6
Source dataset
uspto-grants-1987_05
Patent number
US04666914

Reaction notes

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