Water → 1-Methyl-3-(8-nonenyl)thymine

HRID 1870848Notes

Reaction equation

HRID 1870848 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>[CH2:22]([N:7]1[C:8](=[O:9])[C:10]([CH3:11])=[CH:12][N:4]([CH3:3])[C:5]1=[O:6])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14]

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 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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, available from Alfebro) was added and the resulting mixture stirred for 20 hours. The reaction was poured into water (40 ml) and extracted with three 50 ml aliquots of dichloromethane. The organic layers were combined, washed with water (40 ml) and saturated aqueous salt solution (20 ml). After drying the washed organic layers over sodium sulfate, the solvent was evaporated, leaving a colorless oil, 3-(8-nonenyl)-1-methylthymine, which solidified upon standing (2.76 g, 73% yield).

Workup

  1. extractionextracted with three 50 ml aliquots of dichloromethane
  2. washwashed with water (40 ml) and saturated aqueous salt solution (20 ml)
  3. dry with materialAfter drying the washed organic layers over sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0d0487acae7b4891a112ae336d203aca
Source dataset
uspto-grants-2000_08
Patent number
US06100271

Reaction notes

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