Sodium Hydroxide → 1-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-uracil

HRID 1516770Notes

Reaction equation

HRID 1516770 reaction equation
CC1(C)[O:7][CH2:6][CH:5]([CH2:8][CH2:9][N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:4][O:3]1.[OH-].[Na+]>Cl>[OH:3][CH2:4][CH:5]([CH2:6][OH:7])[CH2:8][CH2:9][N:10]1[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]1=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 578389791-[2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethyl]uracil

Product 1

HCID 2896501-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-uracilYield 35.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 17 (7.75 gm, 30.5 mmol) in 1M HCl (25 ml) was stirred at 25° C. for 30 min. The solution was neutralized by addition of 10% aq. NaOH. The resulting solution was filtered and evaporated under vacuo. The solid residue obtained was chromatographed on a silica gel column using dichloromethane-methanol (88:12, v/v) as eluent to yield 18 (2.3 gm, 35.2%), which was used in the next reaction step.

Workup

  1. filtrationThe resulting solution was filtered
  2. customevaporated under vacuo
  3. customThe solid residue obtained
  4. customwas chromatographed on a silica gel column

Sources & evidence

ORD record
ord-5c006519a6734066a7f698e556494aad
Source dataset
uspto-grants-2012_07
Patent number
US08227594B2

Reaction notes

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