Cyclobutylamine → N-Cyclobutyl-2-fluoro-9-isopropyl-9H-purin-6-amine

HRID 2047666Notes

Reaction equation

HRID 2047666 reaction equation
Cl[C:2]1[N:10]=[C:9]([F:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]([CH3:14])[CH3:13].C(N(C(C)C)CC)(C)C.[CH:24]1([NH2:28])[CH2:27][CH2:26][CH2:25]1>C(O)C>[CH:24]1([NH:28][C:2]2[N:10]=[C:9]([F:11])[N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:12]([CH3:14])[CH3:13])[CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 75645CyclobutylamineHCID 81531DiisopropylethylamineHCID 112873616-Chloro-2-fluoro-9-isopropyl-9H-purine

Product 1

HCID 59279642N-Cyclobutyl-2-fluoro-9-isopropyl-9H-purin-6-amineYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-chloro-2-fluoro-9-isopropyl-9H-purine (0.3 g, 1.4 mmol), diisopropylethylamine (0.2 g, 1.55 mmol) and cyclobutylamine (0.2 g, 2.8 mmol) were stirred together in ethanol (30 ml) at room temperature for 6 h. Volatiles were removed and the residue taken up in ethyl acetate, washed with water (50 ml), brine (50 ml), dried (MgSO4) and concentrated. The crude was purified by silica gel flash column chromatography (ethyl acetate:hexane 3:2) to give the pure product (237 mg, 68%) δH (CDCl3, 500 MHz) 1.56 (6H, d, J 7.5, CH[CH3]2), 1.76-1.74 (2 H, m, CH2 of Cyclobutyl), 1.98-1.94 (2 H, m, CH2 of cyclobutyl), 2.45 (2 H, s, br, CH2 of cyclobutyl)) 4.72-4.7 (2 H, m, CH of cyclobutyl and CHMe2), 6.35 (1 H, s, br, NH), 7.75 (1 H, s, ArH); δC (CDCl3, 500 MHz) 160.08 (C), 158.43 (C), 155.34 (C), 155.18 (C), 150.09 (C), 137.44 (CH), 47.26 (CH), 31.56 (2×CH2), 22.38 (2×CH3), 15.09 (CH2); m/z 250.2 (M+H)

Workup

  1. customVolatiles were 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 flash column chromatography (ethyl acetate:hexane 3:2)

Sources & evidence

ORD record
ord-463bc06cf2594baa8510b12b7171fa04
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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