Hydrochloric Acid → HCID 178508220, compound

HRID 2380571Notes

Reaction equation

HRID 2380571 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:14][C@H:13]([CH2:15][OH:16])[CH2:12]2)=[C:4]([O:17]CC2C=CC=CC=2)[N:3]=1.Cl.CN(C)C=O>CO.O>[NH2:1][C:2]1[NH:3][C:4](=[O:17])[C:5]2[N:6]=[CH:7][N:8]([C@H:11]3[CH2:14][C@@H:13]([CH2:15][OH:16])[CH2:12]3)[C:9]=2[N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 178508944HCID 178508944, compound

Product 1

HCID 178508220HCID 178508220, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of the above preparation of (cis)-3-[2-amino-6-(phenylmethoxy)-9H-purin-9-yl]-cyclobutanemethanol (330 mg) in 5.2 ml of methanol was added 2.6 ml of 3N HCl. The mixture was stirred under nitrogen at 40° for 2 hours and concentrated in vacuo to a solid, which was suspended in water. The pH was adjusted to 7.0 using 1N KOH, and the water was removed in vacuo leaving a solid. Chromatography of this solid on 80 ml of CHP-20P resin (Mitsubishi Chemical Industries) water and then 5% dimethylformamide in water gave 140 mg of (cis)-2-amino-1,9-dihydro-9-[3-(hydroxymethyl)cyclobutyl]-6H-purin-6-one as a solid having m.p. 275°-278° (dec.).

Workup

  1. concentrationconcentrated in vacuo to a solid, which
  2. customthe water was removed in vacuo
  3. customleaving a solid

Sources & evidence

ORD record
ord-b5ec53b102a343888c794494d7712e3c
Source dataset
uspto-grants-1994_11
Patent number
US05369098

Reaction notes

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