Isopropyl iodide → 2,6-dichloro-9-(propan-2-yl)-9H-purine

HRID 1422469Notes

Reaction equation

HRID 1422469 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([Cl:11])[N:3]=1.[H-].[Na+].I[CH:15]([CH3:17])[CH3:16]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:15]([CH3:17])[CH3:16])=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 1784188752,6-dichloro-1H-purine

Product 1

HCID 112184902,6-dichloro-9-(propan-2-yl)-9H-purine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2,6-dichloro-9H-purine (a) (6.0 mmol) dissolved in anhydrous DMF (5.0 mL) was slowly added sodium hydride (7.8 mmol) with stirring at rt over 2 hr. 2-iodopropane was added and the mixture was stirred for 16 hr. The mixture was concentrated. The residue was purified by column chromatography on silica gel, eluting with hexane/EtOAc (20:1 to 3:1) to afford the title compound as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.15 (s, 1H), 4.91 (m, 1H), 1.63 (d, 6H).

Workup

  1. stirringthe mixture was stirred for 16 hr
  2. concentrationThe mixture was concentrated
  3. customThe residue was purified by column chromatography on silica gel
  4. washeluting with hexane/EtOAc (20:1 to 3:1)

Sources & evidence

ORD record
ord-e1c3fd7163b5402298295ec86e6c8549
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

Loading…