Adenine → 9-(4-nitro-phenyl)-9H-purin-6-ylamine

HRID 1912859Notes

Reaction equation

HRID 1912859 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.CC(C)([O-])C.[K+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>CS(C)=O.O>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([N:5]2[CH:6]=[N:7][C:8]3[C:4]2=[N:3][CH:2]=[N:1][C:9]=3[NH2:10])=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

6

Reactant 3

HCID 190AdenineHCID 9590p-FluoronitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 3090939-(4-nitro-phenyl)-9H-purin-6-ylamineYield 93.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In 100 ml of dimethyl sulfoxide, 4.05 g (30.0 mmol) of adenine was dissolved, and 3.5 g (31.0 mmol) of potassium tert-butoxide and 5.0 g (35.0 mmol) of 4-fluoronitrobenzene were added thereto, and the mixture solution was stirred at 80° C. for three hours. The solution was diluted with 200 mL of water and the precipitate formed was collected by filtration, washed with 100 mL of water and 30 mL of methanol in the order named and vacuum dried to obtain 7.2 g (84%) of a target product as a yellow solid.

Workup

  1. customthe precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with 100 mL of water and 30 mL of methanol in the order
  4. customvacuum dried

Sources & evidence

ORD record
ord-fc675b0af2b8458d801a87703d3d2378
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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