Water → 9-(4-Hydroxy-2-(hydroxymethyl)butyl)guanine

HRID 2291848Notes

Reaction equation

HRID 2291848 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]([O:20]C)=O)[C:13](OC)=[O:14])=[C:4](Cl)[N:3]=1.[BH4-].[Li+].[OH2:25]>C(O)(C)(C)C>[OH:20][CH2:18][CH2:17][CH:12]([CH2:13][OH:14])[CH2:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:25])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 19027590Dimethyl 2-(2-amino-6-chloropurin-9-ylmethyl)succinate

Product 1

HCID 1354364559-(4-Hydroxy-2-(hydroxymethyl)butyl)guanine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Dimethyl 2-(2-amino-6-chloropurin-9-ylmethyl)succinate (8.00 g, 0.0244 mol) was dissolved in 200 ml of tert. butanol at 50° C., lithium borohydride (2.66 g, 0.122 mol) was added in portions, and the mixture was stirred for 1 h. Then 100 ml of water was added and the stirring was continued over-night, the inorganic salts were filtered off and the solution was evaporated to dryness in vacuum. The residue was found to contain 78 mole-% of 2-amino-6-tert.butoxy-9-[4-hydroxy-2(hydroxymethyl)butyl]purine together with the 6-chloro compound.

Workup

  1. waitthe stirring was continued over-night
  2. filtrationthe inorganic salts were filtered off
  3. customthe solution was evaporated to dryness in vacuum

Sources & evidence

ORD record
ord-f778431fc16a43ca882734f900f91010
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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