Dimethylformamide → 2-Amino-6-bromopurine

HRID 274318Notes

Reaction equation

HRID 274318 reaction equation
P(Br)(Br)([Br:3])=O.CN(C)C=O.[NH:11]1[C:20](=O)[C:19]2[NH:18][CH:17]=[N:16][C:15]=2[N:14]=[C:12]1[NH2:13]>O>[NH2:13][C:12]1[N:14]=[C:15]2[C:19]([NH:18][CH:17]=[N:16]2)=[C:20]([Br:3])[N:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24613Phosphorus oxybromideHCID 135398634Guanine

Product 1

HCID 61011392-Amino-6-bromopurineYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

86.0 g (0.3 mol) of phosphorus oxybromide was added to 73.1 g (1.0 mol) of N,N-dimethylformamide, and 15.1 g (0.1 mol)of guanine (manufactured by Sumika Fine Chemicals Co., Ltd.) was then added, followed by stirring at 100° C. for 4 hours. After cooling, 200 ml of water was carefully added at 20° C. After stirring at room temperature for 24 hours, the precipitating crystal was collected by filtration and dissolved in 200 ml of 25% aqueous ammonia with heating, and the insoluble substances were filtered out. The mother liquor was concentrated under reduced pressure, and the precipitating crystal was collected by filtration to yield 11.1 g (0.052 mol) of a pale yellow crystal of 2-amino-6-bromopurine (yield 52%). Its properties are as follows:

Workup

  1. additionwas then added
  2. temperatureAfter cooling
  3. stirringAfter stirring at room temperature for 24 hours
  4. filtrationthe precipitating crystal was collected by filtration
  5. dissolutiondissolved in 200 ml of 25% aqueous ammonia
  6. temperaturewith heating
  7. filtrationthe insoluble substances were filtered out
  8. concentrationThe mother liquor was concentrated under reduced pressure
  9. filtrationthe precipitating crystal was collected by filtration

Sources & evidence

ORD record
ord-7081017fabe04acea5e84660f008f41c
Source dataset
uspto-grants-1995_02
Patent number
US05389637

Reaction notes

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