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

HRID 1252681Notes

Reaction equation

HRID 1252681 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 acetonitrile 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 acetonitrile

Sources & evidence

ORD record
ord-7e1638f9fe01443a90d57795846ab7ab
Source dataset
uspto-grants-1988_05
Patent number
US04745119

Reaction notes

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