Water → 1-Methyl-3-(8-nonenyl)thymine

HRID 1954136Notes

Reaction equation

HRID 1954136 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH:12]=[C:10]([CH3:11])[C:8](=[O:9])[NH:7][C:5]1=[O:6].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22].O>CS(C)=O>[CH3:3][N:4]1[CH:12]=[C:10]([CH3:11])[C:8](=[O:9])[N:7]([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14])[C:5]1=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 959611,5-Dimethyl-2,4(1H,3H)-pyrimidinedioneHCID 110199989-Bromo-1-nonene

Product 1

HCID 232958901-Methyl-3-(8-nonenyl)thymineYield 74.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This example illustrates a synthesis of 1-Methyl-3-(8,9-oxidononyl)thymine (inventive compound no. 1910). Sodium hydride (343 mg, 14 mmol) was added to a stirring solution of 1-methylthymine (2.00 g, 14 mmol) in dimethylsulfoxide (40 mL). After 15 minutes, 9-bromo-1-nonene (2.93 g, 14 mmol) was added and the mixture stirred for 20 hours. The reaction was poured into 40 mL water and extracted with dichloromethane (3×50 mL). The organic layers were combined, washed with water (40 mL), saturated aqueous salt solution (20 mL), and dried over sodium sulfate. The solvent was evaporated to yield 2.76 g (73% yield) 1-Methyl-3-(8-nonenyl)thymine (inventive compound no. 1917) as a colorless oil which solidified upon standing.

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. washwashed with water (40 mL), saturated aqueous salt solution (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-adc3e628dca74e09ae29d6762e9a30d9
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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