tert-Butanol → HCID 406593, compound

HRID 2256823Notes

Reaction equation

HRID 2256823 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]([CH2:11][CH:12]([CH2:17][C:18](OC)=[O:19])[C:13](OC)=[O:14])[CH:6]=[N:7]2)=[N:3][CH:2]=1.C(O)(C)(C)C.[BH4-].[Li+]>O>[OH:19][CH2:18][CH2:17][CH:12]([CH2:13][OH:14])[CH2:11][N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 4148881Lithium borohydrideHCID 19027594HCID 19027594, compound

Product 1

HCID 406593HCID 406593, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl 2-(adenine-9-ylmethyl)succinate (2.93 g, 0.010 mol) was dissolved by warming with tert. butanol (120 ml), lithium borohydride (1.10 g, 0.05 mol) was added in portions and the mixture was stirred at ambient temperature for 3 h, water (10 ml) was added and stirring was continued over night. Inorganic material was filtered off and washed with tert. butanol and the filtrate evaporated to small volume. Chromatography on silica (ethyl acetate+methanol+water 7+2+1) afforded pure 9-(4-hydroxy-2-hydroxymethylbutyl) adenine.

Workup

  1. additionwas added in portions
  2. stirringstirring
  3. waitwas continued over night
  4. filtrationInorganic material was filtered off
  5. washwashed with tert. butanol
  6. customthe filtrate evaporated to small volume

Sources & evidence

ORD record
ord-fc972f52a4a24106885c88f40c9b02be
Source dataset
uspto-grants-1997_08
Patent number
US05656617

Reaction notes

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