Sodium Cyanide → 9-(2,2-dimethyl-propyl)-8-methyl-9H-purine-2-carbonitrile

HRID 271627Notes

Reaction equation

HRID 271627 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH3:16])[N:8]2[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][N:3]=1.[C-]#N.[Na+].C1N2CC[N:22](CC2)[CH2:21]1>CS(C)=O.O>[CH3:13][C:12]([CH3:15])([CH3:14])[CH2:11][N:8]1[C:7]([CH3:16])=[N:6][C:5]2[C:9]1=[N:10][C:2]([C:21]#[N:22])=[N:3][CH:4]=2

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 9237DabcoHCID 179682662-chloro-9-(2,2-dimethyl-propyl)-8-methyl-9H-purine

Product 1

HCID 179682149-(2,2-dimethyl-propyl)-8-methyl-9H-purine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Procedure

6.1 g of 2-chloro-9-(2,2-dimethyl-propyl)-8-methyl-9H-purine, 1.25 g of NaCN and 0.57 g of DABCO were heated for 6 hours to 80° C. in 60 ml DMSO/H2O=90:10. The crude mixture was extracted with ethyl acetate and saturated NaHCO3 solution and the organic phases were dried over sodium sulfate and evaporated to dryness. After chromatography on silicagel with ethyl acetate/hexanes=1:1 9-(2,2-dimethyl-propyl)-8-methyl-9H-purine-2-carbonitrile was isolated as a pale brown powder.

Workup

  1. extractionThe crude mixture was extracted with ethyl acetate and saturated NaHCO3 solution
  2. dry with materialthe organic phases were dried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-432b637e35b8464f8f30fa9afc28a28d
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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