Sodium Cyanide → HCID 9883178, compound

HRID 1162982Notes

Reaction equation

HRID 1162982 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1.[C-:23]#[N:24].[Na+]>CN(C=O)C>[CH:17]1([NH:16][C:4]2[N:3]=[C:2]([C:23]#[N:24])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 11359100HCID 11359100, compound

Product 1

HCID 9883178HCID 9883178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-6-cyclohexylamino-9-cyclopentyl-purine (6.3 mmol) and sodium cyanide (36 mmol) are heated up in DMF (30 ml) to 160° C. for 70 hours. After cooling down to RT the mixture is poured on water and extracted 3 times with ethyl acetate. The combined organic phases are washed with brine and the extract is dried over sodium sulfate and evaporated. The residue is purified by flash chromatography on silica gel with ethyl acetate as mobile phase. The product containing fractions are combined and evaporated. A pale yellow oil with Rf=0.33 (ethyl acetate) is obtained.

Workup

  1. additionis poured on water
  2. extractionextracted 3 times with ethyl acetate
  3. washThe combined organic phases are washed with brine
  4. dry with materialthe extract is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is purified by flash chromatography on silica gel with ethyl acetate as mobile phase
  7. additionThe product containing fractions
  8. customevaporated
  9. customA pale yellow oil with Rf=0.33 (ethyl acetate) is obtained

Sources & evidence

ORD record
ord-52675b1d32884617b778ad2c2cc83182
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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