Methylamine → 1,3-Propanediol, 2-[(2-amino-9H-purin-9-yl)methoxy]-

HRID 64626Notes

Reaction equation

HRID 64626 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[CH2:14][O:15]C(=O)C2C=CC=CC=2)=[CH:4][N:3]=1.CN>>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH:13]([CH2:14][OH:15])[CH2:24][OH:25])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 137140202-Amino-9-[(2-benzoyloxy-1-(benzoyloxymethyl)ethoxy)methyl]-9H-purine

Product 1

HCID 30100981,3-Propanediol, 2-[(2-amino-9H-purin-9-yl)methoxy]-

Procedure

A mixture of 0.844 g (1.88 mM) of 2-amino-9-[(2-benzoyloxyl-1-(benzoyloxymethyl)ethoxy)methyl]-9H-purine and 100 ml of a 40% aqueous methylamine solution was stirred at room temperature for 30 minutes. The mixture was flash evaporated to a yellow oil which was then washed with water. The aqueous layer was then extracted twice with methylene chloride. The aqueous layer containing the product was then flash evaporated to a light yellow oil. Recrystallization of the oil in hot acetonirile yielded the title compound as an analytically pure ivory solid, mpt. 148°-151°.

Workup

  1. customevaporated to a yellow oil which
  2. washwas then washed with water
  3. extractionThe aqueous layer was then extracted twice with methylene chloride
  4. additionThe aqueous layer containing the product
  5. customflash evaporated to a light yellow oil
  6. customRecrystallization of the oil in hot acetonirile

Sources & evidence

ORD record
ord-c977741a645a4c32bcc7211676aecbf6
Source dataset
uspto-grants-1986_09
Patent number
US04609662

Reaction notes

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