Isopropyl iodide → 6-Chloro-2-fluoro-9-isopropyl-9H-purine

HRID 2047663Notes

Reaction equation

HRID 2047663 reaction equation
[F:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:18](I)([CH3:20])[CH3:19]>CN(C=O)C>[Cl:11][C:4]1[N:3]=[C:2]([F:1])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH:18]([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 52879146-Chloro-2-fluoropurine

Product 1

HCID 112873616-Chloro-2-fluoro-9-isopropyl-9H-purineYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-fluoro,6-chloro-purine (2 g, 11.7 mmol), and powdered potassium carbonate (4 g, 28 mmol) was vigorously stirred in 30 ml DMF. Isopropyliodide (6 ml, 60 mmol) was added very slowly over 2 h. The reaction was stirred for a further 5 h. DMF was removed and the crude taken up in ethyl acetate, washed with water (50 ml), brine (50 ml), dried (MgSO4) and concentrated. The crude was purified by silica gel column chromatography (30% ethyl acetate in hexane) to provide the pure product as a white solid (1.1 g, 44%). δH (CD3OD, 250 MHz) 1.65 [6 H, d, J 7.5, CH(CH3)2], 4.92 [1 H, m, CH(CH3)2], 8.66 (1 H, s, ArH); δC (CD3OD, 250 MHz) 154.7 (C), 153.88 (C), 152.2 (C), 147.65 (CH), 132.44 (C), 50.66 (CH), 22.72 (2×CH3); m/z 215.2 (M+H)

Workup

  1. customDMF was removed
  2. washwashed with water (50 ml), brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude was purified by silica gel column chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-23a4da5c47bc43188589ebf30dd5e468
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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