Water → 2-(2-Aminopurin-9-yl)methyl butan-1,4-diol

HRID 864987Notes

Reaction equation

HRID 864987 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]([CH2:17][C:18](OC)=[O:19])[C:13](OC)=[O:14])=[CH:4][N:3]=1.[BH4-].[Li+].O>C(O)(C)(C)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]([CH2:17][CH2:18][OH:19])[CH2:13][OH:14])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 19027589Dimethyl (2-aminopurin-9-ylmethyl)succinate

Product 1

HCID 146200082-(2-Aminopurin-9-yl)methyl butan-1,4-diol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of crude dimethyl (2-aminopurin-9-ylmethyl)succinate (3.2 g, 10.9 mmol), dissolved in tert. butanol (250 ml) at 40° C., was added lithium borohydride (1.3 g, 60 mmol) in portions with stirring. After 1 hour at ambient temperature, water (30 ml) was added slowly and stirring continued over night. Inorganic salts were filtered and the solution evaporated to dryness. Yield of crude product was 1.6 g (50%). Chromatography on silica (chloroform+methanol 7+1) afforded pure product.

Workup

  1. stirringstirring
  2. waitcontinued over night
  3. filtrationInorganic salts were filtered
  4. customthe solution evaporated to dryness
  5. customChromatography on silica (chloroform+methanol 7+1) afforded pure product

Sources & evidence

ORD record
ord-225b8e07cc1d4468948ef84dd06751ba
Source dataset
uspto-grants-1996_10
Patent number
US05565461

Reaction notes

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