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

HRID 1422478Notes

Reaction equation

HRID 1422478 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.C(I)[I:18].N(OCCC(C)C)=O.C(=O)(O)[O-].[Na+]>C1COCC1.[Cu]I>[Cl:1][C:2]1[N:10]=[C:9]([I:18])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]([CH3:14])[CH3:13]

Participants

8

Reactant 5

HCID 807IodineHCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 516892Sodium BicarbonateHCID 219337716-Chloro-9-isopropyl-9h-purin-2-amine

Product 1

HCID 65389046-Chloro-2-iodo-9-isopropyl-9H-purine

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-amine (2.68 g, 12.7 mmol) was dissolved in THF (64 mL) at rt. Iodine (1.61 g, 6.25 mmol), CH2I2 (10.6 mL) and CuI (1.27 g, 6.66 mmol) were added. The mixture was stirred for 5 min at room temperature. Isopentyl nitrite (5.33 mL) was added. The reaction mixture was refluxed for 45 min, and was then cooled to room temperature. Saturated aqueous sodium bicarbonate solution was added, and the mixture was extracted with EtOAc three times. The combined organic phase was washed with brine, dried with MgSO4 and concentrated. The residue was purified by column chromatography on silica gel, eluting with 0 to 30% ethyl acetate in hexane to afford the title compound as a solid. 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 4.95-4.88 (m, 1H), 1.65 (d, 6H). MS m/z 323.0 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 45 min
  2. temperaturewas then cooled to room temperature
  3. extractionthe mixture was extracted with EtOAc three times
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with 0 to 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1531000c6b9246cabcdd91027c75b2ed
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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