Dimethylformamide → 2-Amino-6-chloropurine

HRID 274315Notes

Reaction equation

HRID 274315 reaction equation
P(Cl)(Cl)([Cl: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]([Cl:3])[N:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 135398634Guanine

Product 1

HCID 53603492-Amino-6-chloropurineYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

46.0 g (0.3 mol) of phosphorus oxychloride 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, 100 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 100 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 9.3 g (0.055 mol) of a white crystal of 2-amino-6-chloropurine (yield 55%).

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 100 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-89ca48dd27514a93b9638772809d5a87
Source dataset
uspto-grants-1995_02
Patent number
US05389637

Reaction notes

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