Isopropyl iodide → 6-Chloro-9-isopropyl-9h-purin-2-amine

HRID 1422477Notes

Reaction equation

HRID 1422477 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][NH:10]2)=[C:6]([Cl:13])[N:5]=1.I[CH:15]([CH3:17])[CH3:16]>CN(C=O)C>[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[CH:15]([CH3:17])[CH3:16])=[C:6]([Cl:13])[N:5]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 1785084356-chloro-1H-purin-2-amine

Product 1

HCID 219337716-Chloro-9-isopropyl-9h-purin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.5 g of 60% dispersion in mineral oil, 38 mmol) was added in portions over 10 min to a stirred suspension of 2-amino-6-chloro-9H-purine (5.34 g, 31.5 mmol) in anhydrous DMF (50 mL) at rt. After 45 min, the mixture was cooled in an ice bath, then 2-iodopropane was added. The cooling bath was removed and the stirred mixture was allowed to warm to rt over 16 h. The mixture was cooled in ice, then water was added. The mixture was concentrated, and the residue was treated with hot ethyl acetate. The cooled mixture was filtered, and the filtrate was concentrated. The residue was purified by column chromatography on silica gel, eluting with 0 to 50% EtOAc in hexane to afford the title compound as a solid. 1H NMR (400 MHz, CDCl3) δ 7.83 (s, 1H), 5.17 (s, 2H), 4.71-4.66 (m, 1H), 1.57 (d, 6H). MS m/z 212.1 (M+1).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customThe cooling bath was removed
  3. temperatureThe mixture was cooled in ice
  4. additionwater was added
  5. concentrationThe mixture was concentrated
  6. additionthe residue was treated with hot ethyl acetate
  7. filtrationThe cooled mixture was filtered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with 0 to 50% EtOAc in hexane

Sources & evidence

ORD record
ord-c568da62b92444bd930e271703c4eb3a
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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