Sodium Methoxide → 1,3-Propanediol, 2-[(2-amino-6-chloro-9H-purin-9-yl)methoxy]-

HRID 330589Notes

Reaction equation

HRID 330589 reaction equation
C([O:4][CH2:5][CH:6]([O:12][CH2:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][C:17]([NH2:24])=[N:18][C:19]=2[Cl:23])[CH2:7][O:8]C(=O)C)(=O)C.C[O-].[Na+]>CO>[OH:4][CH2:5][CH:6]([O:12][CH2:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][C:17]([NH2:24])=[N:18][C:19]=2[Cl:23])[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 137128349-(1,3-Diacetoxy-2-propoxymethyl)-2-amino-6-chloropurine

Product 1

HCID 110766071,3-Propanediol, 2-[(2-amino-6-chloro-9H-purin-9-yl)methoxy]-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 781 mg (2.18 mmoles) of 9-(1,3-diacetoxy-2-propoxymethyl)-2-amino-6-chloropurine in 22 ml of methanol was treated with 109 mmoles (5 mole percent) of freshly prepared sodium methoxide. Within ten minutes the stirred solution became cloudy and the product precipitated gradually in the course of forty-five minutes. The product was isolated by filtration, washed with 10 ml of water and dried in vacuo over P2O5 yielding 507 mg of pure product. A 200 MHz nmr spectrum in d6DMSO was fully in accord with the structure.

Workup

  1. waitWithin ten minutes the stirred solution became
  2. customcloudy and the product precipitated gradually in the course of forty-five minutes
  3. customThe product was isolated by filtration
  4. washwashed with 10 ml of water
  5. dry with materialdried in vacuo over P2O5 yielding 507 mg of pure product

Sources & evidence

ORD record
ord-6eec0f82ce6c4a6da11d513fd92f9d38
Source dataset
uspto-grants-1990_01
Patent number
US04897479

Reaction notes

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