Iodine → 6-Chloro-2-iodo-9-isopropyl-9H-purine

HRID 1241344Notes

Reaction equation

HRID 1241344 reaction equation
[Cl:1][C:2]1[N:10]=[C:9](N)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]([CH3:14])[CH3:13].II.N(OCCC(C)C)=O.C(I)[I:26]>C1COCC1.[Cu]I>[Cl:1][C:2]1[N:10]=[C:9]([I:26])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 807IodineHCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 219337716-Chloro-9-isopropyl-9h-purin-2-amine

Product 1

HCID 65389046-Chloro-2-iodo-9-isopropyl-9H-purineYield 324.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-9-isopropyl-9H-purin-2-ylamine (2.7 g, 12.8 mmol), CuI (1.2 g, 13.4 mmol), I2 (3.3 g, 12.8 mmol), isoamyl nitrite (10.6 mL), and CH2I2 (5.3 g, 39.3 mmol) in THF (60 mL) were heated at reflux for 75 min. The mixture was cooled to rt, filtered through Celite, and adsorbed onto silica gel. Purification by chromatography (60% EtOAc/hexane) yielded an off-white solid (13.4 g, 54%): MS [M+H]+ 323; m.p.104° C.

Workup

  1. temperatureat reflux for 75 min
  2. filtrationfiltered through Celite
  3. customPurification by chromatography (60% EtOAc/hexane)

Sources & evidence

ORD record
ord-7c58faed018d4b658eff37db9f430a0d
Source dataset
uspto-grants-2006_10
Patent number
US07115589B2

Reaction notes

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