Water → 6-((2,2-Diphenylethyl)amino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carbonitrile

HRID 2268407Notes

Reaction equation

HRID 2268407 reaction equation
[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17](S(C)(=O)=O)[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:35]#[N:36].[K+].O>CN(C)C=O>[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:35]#[N:36])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 21978255N-(2,2-Diphenylethyl)-2-(methylsulphonyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

Product 1

HCID 101593916-((2,2-Diphenylethyl)amino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carbonitrileYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A stirred solution of N-(2,2-diphenylethyl)-2-(methylsulfonyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine (preparation 8) (20.1 g, 42.1 mmol) in dry N,N-dimethylformamide (100 ml) was treated with potassium cyanide (5.5 g, 84.6 mmol) and the mixture heated at 120° C. for 24 hr under a nitrogen atmosphere. The mixture was then cooled to room temperature, poured into water (1000 ml) and stirring continued for a further 1 hr. The resultant solid was slowly filtered and washed several times with water, then dissolved in dichloromethane. The solution washed with water, dried with anhydrous magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was then dissolved in diethyl ether and the solvent removed under reduced pressure (repeated) to afford the title compound as an oil (17 g).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationThe resultant solid was slowly filtered
  3. washwashed several times with water
  4. dissolutiondissolved in dichloromethane
  5. washThe solution washed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. dissolutionThe residue was then dissolved in diethyl ether
  10. customthe solvent removed under reduced pressure (repeated)

Sources & evidence

ORD record
ord-41a728a4583142b68fb252b0fa628139
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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