Sodium Azide → 1-(3-Azidomethyl-4-hydroxybutyl)-1H-pyrimidine-2,4-dione

HRID 1713378Notes

Reaction equation

Br[CH2:2][CH:3]([CH2:14][OH:15])[CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]1=[O:13].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C>[N:16]([CH2:2][CH:3]([CH2:14][OH:15])[CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]1=[O:13])=[N+:17]=[N-:18]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of compound 38 (10.9 g, 0.042 mol) in dry DMF (40 mL) was treated with NaN3 (4.1 g, 0.062 mol) and heated to 70° C. for 24 h. The reaction mixture was concentrated under vacuum and crude purified by column chromatography over silica gel (30% methanol in chloroform) to give the title compound (5.2 g, 47%). TLC: Chloroform/Methanol, 1:1, Rf=0.2

Workup

concentrationThe reaction mixture was concentrated under vacuum and crude
custompurified by column chromatography over silica gel (30% methanol in chloroform)

Sources & evidence

ORD record: ord-7982a509f2a245fb8e39c3ead38acc58
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795270B2

Reaction notes

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