Acetic Acid → 8-Bromo-9-methyl-9H-adenine

HRID 1901235Notes

Reaction equation

HRID 1901235 reaction equation
[CH3:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[NH2:11].C([O-])(=O)C.[Na+].C(O)(=O)C.[Br:21]Br>O>[Br:21][C:10]1[N:2]([CH3:1])[C:3]2[C:8]([N:9]=1)=[C:7]([NH2:11])[N:6]=[CH:5][N:4]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 696899-MethyladenineHCID 517045Sodium Acetate

Product 1

HCID 8222968-Bromo-9-methyl-9H-adenine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Fifteen grams (0.1 mol) of 9-methyladenine of Example 1 was dissolved in 1.5 liters of buffer prepared from 30.8 g of sodium acetate, 1.4 liters of water and sufficient acetic acid to provide a pH of 4.0. To this solution was added dropwise 25 ml of bromine in 2 liters of water over a period of two hours. The reaction was stirred a further two hours and the resulting solid filtered off and rinsed with the water. The solid was air dried and warmed to about 50° in about 80 ml of methanol, stripped to a hazy suspension and filtered. The precipitate after rinsing with water and drying at 40° under vacuum overnight weighed 15.6 g. The filtrate was stripped of methanol and a further 1.6 g was collected. The combined solids were triturated in about 100 ml of acetone for three hours and then allowed to sit overnight. The resulting precipitate was filtered and washed with acetone to yield 13.3 g after drying at 40° on a vacuum pump overnight.

Workup

  1. customto provide a pH of 4.0
  2. filtrationthe resulting solid filtered off
  3. washrinsed with the water
  4. customdried
  5. temperaturewarmed to about 50° in about 80 ml of methanol
  6. filtrationfiltered
  7. washThe precipitate after rinsing with water
  8. customdrying at 40° under vacuum overnight
  9. customa further 1.6 g was collected
  10. customThe combined solids were triturated in about 100 ml of acetone for three hours
  11. waitto sit overnight
  12. filtrationThe resulting precipitate was filtered
  13. washwashed with acetone
  14. customto yield 13.3 g
  15. customafter drying at 40° on a vacuum pump overnight

Sources & evidence

ORD record
ord-09f77ac83825413fa8a7d3905d95228e
Source dataset
uspto-grants-1996_11
Patent number
US05576427

Reaction notes

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