9-(2-Chloroethyl)-9H-purin-6-amine → HCID 69641888, compound

HRID 889849Notes

Reaction equation

HRID 889849 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][CH:7]=[N:8][C:9]=2[NH2:13].[CH3:14][NH:15][CH:16]([OH:18])[CH3:17]>C(O)CCC>[NH2:13][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[C:10]=1[N:11]=[CH:12][N:4]2[CH2:3][CH2:2][N:15]([CH:16]([OH:18])[CH3:17])[CH3:14]

Participants

4

Reactant 2

HCID 2422639-(2-Chloroethyl)-9H-purin-6-amineHCID 5247031N-Methylaminoethanol

Product 1

HCID 69641888HCID 69641888, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

0.6 g (3 mmol) 9-(chloroethyl)-6-amino-9H-purine (Chemistry of Heterocyclic Compounds, 1996, 32, 333–337) was dissolved in 10 ml n-butanol and treated with 0.684 g (9 mmol) of N-methylaminoethanol at 110° C. for 18 h. The solvent was evaporated under reduced pressure and the crude mixture purified by flash chromatography on silica gel with a gradient of 0 to 25% methanol in dichloromethane to yield 0.68 g (94%) of a light orange solid. MS (ISP): 237.3 (MH+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude mixture purified by flash chromatography on silica gel with a gradient of 0 to 25% methanol in dichloromethane

Sources & evidence

ORD record
ord-9e5c556b54944379a3d5e350f9de099b
Source dataset
uspto-grants-2006_02
Patent number
US06995143B2

Reaction notes

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