Cyclopropanemethanamine → N-(Cyclopropylmethyl)-2-fluoro-9-isopropyl-9H-purine-6-amine

HRID 2047665Notes

Reaction equation

HRID 2047665 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([CH2:27][NH2:28])[CH2:26][CH2:25]1>C(O)C>[CH:24]1([CH2:27][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])[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 112873616-Chloro-2-fluoro-9-isopropyl-9H-purine

Product 1

HCID 57433118N-(Cyclopropylmethyl)-2-fluoro-9-isopropyl-9H-purine-6-amineYield 83.1%

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 cyclopropylmethylamine (0.24 g, 2.7 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 (290 mg, 83%) as a colorless gum. δH (CDCl3, 500 MHz) 0.29-0.27 (2 H, m, CHHCHH of Cp), 0.56-0.54 (2H, m, CHHCHH of Cp), 1.13 (1 H, s, br, CH of Cp), 1.58 (6 H, d, J 7.5, CH[CH3]2), 3.44 (2 H, s, br, NHCH2Cp) 2.97 (1 H, s, br, CH of Cp), 4.74-4.72 (1 H, m, CHMe2), 6.22 (1 H, s, br, NH), 7.76 (1 H, s, ArH); δC (CDCl3, 500 MHz) 160.09 (C), 156.14 (C), 147.4 (C), 137.38 (CH), 118.26 (C), 47.14 (CH), 45.78 (CH2), 22.46 (2×CH3), 10.06 (CH), 3.5 (2×CH2)

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-cf7af753dcb14e34a64cd0bcd1150b7f
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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