Sodium Hydroxide → HCID 22386610, compound

HRID 1072972Notes

Reaction equation

C([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][N:16]1[C:23]([CH2:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=2)=[C:22]([CH2:33][CH3:34])[C:20](=[O:21])[NH:19][C:17]1=[O:18])(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[CH3:32][C:27]1[CH:26]=[C:25]([CH:30]=[C:29]([CH3:31])[CH:28]=1)[CH2:24][C:23]1[N:16]([CH2:15][O:14][CH2:13][CH2:12][CH2:11][CH2:10][OH:9])[C:17](=[O:18])[NH:19][C:20](=[O:21])[C:22]=1[CH2:33][CH3:34]

Participants

Conditions

Temperature: 20 °C

Procedure

1-(4-benzoyloxybutyloxymethyl)-6-(3,5-dimethylbenzyl)-5-ethyluracil (500 mg, 1.08 mmol) was added to a solution of sodium hydroxide (360 mg, 9 mmol) in methanol (50 ml) and the mixture was stirred at 20° C. for 3 h. After neutralization (concentrated hydrochloric acid) and concentration, the residue was subjected to a flash column chromatography (dichloromethane/methanol 19:1) which gave the 6-(3,5-dimethyl benzyl)-5-ethyl-1-(4-hydroxybutyloxymethyl)uracil (190 mg, 48%) in the form of a white solid.

Workup

concentrationAfter neutralization (concentrated hydrochloric acid) and concentration

Sources & evidence

ORD record: ord-699a03f6197744fe88a304be0f6076f3
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06911450B1

Reaction notes

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