Dabco → 9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine-6-carbonitrile

HRID 1246800Notes

Reaction equation

HRID 1246800 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.[N:26]12CCN(CC1)C[CH2:27]2>C(#N)C.[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([N:6]2[C:5]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[C:27]#[N:26])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 9237DabcoHCID 219058016-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine

Product 1

HCID 219057889-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 165872Tetrabutylammonium CyanideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

6-Chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine I-(1A-1)d (200 mg, 0.49 mmol) was dissolved in acetonitrile (5 ml) and stirred at 0° C. Tetrabutylammonium cyanide (236 mg, 0.98 mmol) and 1,4-diaza-bicyclo[2.2.2]octane (173 mg, 1.5 mmol) were added to the reaction mixture and stirring was continued at 0° C. for 3 hours. The reaction mixture was concentrated under reduced pressure and then purified by flash chromatography using 30% ethyl acetate/hexanes as the eluant to obtain the desired product I-(16A-1)a (215 mg, quant): +ESI MS (M+1) 400.2; 1H NMR (400 MHz, CDCl3) δ 9.09 (s, 1H), 7.57 (d, J=8.7 Hz, 1H), 7.45–7.39 (m, 4H), 7.21 (d, J=8.7 Hz, 2H).

Workup

  1. stirringstirring
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1bf80debc1414086a856f7f878b45d7b
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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