Ammonia → 2-Chloro-9-ethyl-9H-purin-6-amine

HRID 457691Notes

Reaction equation

HRID 457691 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4](Cl)[N:3]=1.[NH3:14]>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4]([NH2:14])[N:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 219883252,6-dichloro-9-ethyl-9H-purine

Product 1

HCID 232737382-Chloro-9-ethyl-9H-purin-6-amine

Procedure

A solution of 2,6-dichloro-9-ethylpurine (2.7 g, 12.4 mmol), a compound of formula (2), in liquid ammonia (20 mL) was sealed in a stainless steel tube and set aside at room temperature for 20 hours. The solvent was removed in vacuo and the residue was purified by flash chromatography on a silica gel column eluting with EtOAc-cyclohexane (65:35) to give 2-chloro-9-ethyl-9H-purin-6-ylamine, a compound of formula (3) (2.28 g, 93%) as a chromatographically pure solid: mp 258–262° C.; 1H NMR (Me2SO-d6) δ 1.39 (t, 3H, J=7.3 Hz, CH2CH3), 4.13 (q, 2H, J=7.3 Hz, CH2CH3), 7.74 (s, 2H, NH2), 8.18 (s, 1H, H-8). Anal. (C7H7ClN5) C, H, N.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography on a silica gel column
  3. washeluting with EtOAc-cyclohexane (65:35)

Sources & evidence

ORD record
ord-2ae941610842411eba1d822c188ff30f
Source dataset
uspto-grants-2007_03
Patent number
US07189730B2

Reaction notes

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