Methanol, 1,1-diethoxy-, 1-acetate → 1,4-Anhydro-2-(6-chloro-9H-purin-9-yl)-2,3-dideoxypentitol

HRID 893613Notes

Reaction equation

HRID 893613 reaction equation
[NH2:1][C:2]1[C:3]([NH:9][C@H:10]2[CH2:14][O:13][C@@H:12]([CH2:15][OH:16])[CH2:11]2)=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].[CH2:17](OC(OC(=O)C)OCC)C>>[Cl:8][C:7]1[N:6]=[CH:5][N:4]=[C:3]2[C:2]=1[N:1]=[CH:17][N:9]2[C@H:10]1[CH2:14][O:13][C@@H:12]([CH2:15][OH:16])[CH2:11]1

Participants

3

Reactant 2

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 14606675HCID 14606675, compound2×

Product 1

HCID 1804661,4-Anhydro-2-(6-chloro-9H-purin-9-yl)-2,3-dideoxypentitolYield 48%

Procedure

A solution of (2R-cis)-4-[(5-amino-6-chloro-4-pyrimidinyl)amino]tetrahydro-2-furanmethanol, Compound IX, (220 mg, 0.90 mmole) and diethoxymethylacetate (5 mL) in a 10 mL round bottom flask fitted with a reflux condenser was heated to 100° for 120 hours. The volatile materials were removed via rotary evaporation, and the residue was recombined with toluene (5 mL) and p-toluenesulphonic acid (5 mg). After stirring at room temperature for one hour and by flash column chromatography (10% MeOH/90% CH2Cl2) to afford 109 mg (48%) of Compound X as a white solid:

Workup

  1. temperaturewas heated to 100° for 120 hours
  2. customThe volatile materials were removed via rotary evaporation

Sources & evidence

ORD record
ord-c10a24021f86488e8fbbef8e659d64c7
Source dataset
uspto-grants-1992_06
Patent number
US05126347

Reaction notes

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