Water → HCID 23295976, compound

HRID 361514Notes

Reaction equation

HRID 361514 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH:11]=[CH:10][C:8](=[O:9])[NH:7][C:5]1=[O:6].Br[CH:13]([CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18].O>CS(C)=O>[CH3:3][N:4]1[CH:11]=[CH:10][C:8](=[O:9])[N:7]([CH2:21][CH2:20][CH2:19][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[C:5]1=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 120091-MethyluracilHCID 24758Sodium hydrideHCID 23295975HCID 23295975, compound

Product 1

HCID 23295976HCID 23295976, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This example illustrates a synthesis of 1-Methyl-3-(8,9-oxidononyl)uracil (inventive compound no. 1804). Sodium hydride (365 mg, 16 mmol) was added to a stirring solution of 1-methyluracil (2.00 g, 16 mmol) in dimethyl sulfoxide (40 mL). After 15 minutes, 6-bromo-1-nonene (3.26 g, 16 mmol) was added and the mixture stirred for 3 days. The reaction was then poured into water (50 mL) and extracted with dichloromethane (3×60 mL). The combined organic layers were washed with water (50 mL), and aqueous saturated salt solution (30 mL) was then dried over sodium sulfate. The solvent was evaporated under vacuum to yield 3.72 g (94%) 1-methyl-3-(8-nonenyl)uracil (inventive compound no. 1817) as a colorless oil which solidified upon standing.

Workup

  1. extractionextracted with dichloromethane (3×60 mL)
  2. washThe combined organic layers were washed with water (50 mL), and aqueous saturated salt solution (30 mL)
  3. dry with materialwas then dried over sodium sulfate
  4. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-6144856922ea48d8b80375fbbbdb9e28
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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