Diisobutylaluminumhydride → C-[9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-yl]-methylamine

HRID 1246801Notes

Reaction equation

HRID 1246801 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[C:25]#[N:26])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[CH2:25][NH2:26])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 219057889-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine-6-carbonitrile

Product 1

HCID 21905813C-[9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-yl]-methylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine-6-carbonitrile I-(16A-1)a (110 mg, 0.27 mmol) was dissolved in methylene chloride (0.9 ml) and the solution cooled to −78° C. Diisobutyl aluminum hydride (1 M in methylene chloride; 590 μl, 0.59 mmol) was added dropwise to the reaction mixture and stirring continued at −78° C. until TLC indicated the starting material had been consumed. Methanol (100 μl) was added to the mixture to quench the reaction and the cooling bath was removed. The reaction mixture was extracted with ethyl acetate from 1 M HCl. The organic layer was back-extracted with 1M HCl and the aqueous layers combined. The aqueous layers were then brought to a basic pH with sodium hydroxide and extracted with ethyl acetate. The organic layers were combined, dried (Na2SO4), filtered, and evaporated to dryness to afford the desired compound I-(16A-1)b: +ESI MS (M+1) 404.4; 1H NMR (400 MHz, CD3OD) δ 8.92 (s, 1H), 7.69 (d, J=8.3 Hz, 1H), 7.57 (d, J=1.7 Hz, 1H), 7.53–7.43 (m, 3H), 7.36 (d, J=8.3 Hz, 2H), 4.40 (s, 2H).

Workup

  1. customcontinued at −78° C. until TLC
  2. customhad been consumed
  3. additionMethanol (100 μl) was added to the mixture
  4. customto quench
  5. customthe reaction
  6. customthe cooling bath was removed
  7. extractionThe reaction mixture was extracted with ethyl acetate from 1 M HCl
  8. extractionThe organic layer was back-extracted with 1M HCl
  9. extractionextracted with ethyl acetate
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-04f062ed85c74d88861f06cc3eafcd30
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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