Cyclopropylamine → HCID 59279635, compound

HRID 2047664Notes

Reaction equation

HRID 2047664 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:18]([CH:21]([CH3:23])[CH3:22])CC)(C)C.C1(N)CC1>C(O)C>[CH:21]1([NH:18][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])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 112873616-Chloro-2-fluoro-9-isopropyl-9H-purine

Product 1

HCID 59279635HCID 59279635, compoundYield 70.5%

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 cyclopropylamine (0.2 g, 2.66 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 (232 mg, 70.5%) δH (CDCl3, 500 MHz) 0.63-0.55 (2 H, m, CHHCHH of Cp), 0.85-0.78 (2 H, m, CHHCHH of Cp), 1.54 (6H, d, J 7.5, CH[CH3]2), 2.97 (1 H, s, br, CH of Cp), 4.73-4.62 (1 H, m, CHMe2), 6.72 (1 H, s, br, NH) 7.7 (1 H, s, ArH); δC (CDCl3, 500 MHz) 159.29 (C), 157.63 (C), 156.8 (C), 156.64 (C), 137.69 (CH), 47.35 (CH), 22.6 (2×CH3), 21.06 (CH), 7.28 (2×CH2); m/z 236.2 (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-fc0657a605e24ee1b4c4b4cbf3efc32a
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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