Sodium hydride → 1-Methyl-3-(8-nonenyl)thymine

HRID 1379011Notes

Reaction equation

HRID 1379011 reaction equation
O[CH:2]([CH2:20]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[CH:13][N:12]([CH3:18])[C:11]1=[O:19].[H-].[Na+].CN1C=C(C)C(=O)NC1=O.BrCCCCCCCC=C>CS(C)=O.O>[CH2:9]([N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[CH:13][N:12]([CH3:18])[C:11]1=[O:19])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:20]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 959611,5-Dimethyl-2,4(1H,3H)-pyrimidinedioneHCID 110199989-Bromo-1-noneneHCID 232879543-(8,9-Dihydroxynonyl)-1-methylthymine

Product 1

HCID 232958901-Methyl-3-(8-nonenyl)thymineYield 73%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

3-(8,9-Dihydroxynonyl)-1-methylthymine (CT1918) was used as an intermediate for the synthesis of CT1908 (example 12). A mixture of sodium hydride (343 mg, 14 mmol) and 1-methylthymine (2.00 g, 14 mmol) in dimethylsulfoxide (40 ml) was stirred for 15 min and then 9-bromo-1-nonene (2.93 g, 14 mmol) was added. After stirring for 20 hr, the mixture was poured into water (40 ml) and extracted with dichloromethane (3×50 ml). The combined organic layers were washed with water (40 ml), with saturated aqueous sodium chloride solution (20 ml), and dried over sodium sulfate. The solvent was evaporated to give 3-(8-nonenyl)-1-methylthymine (CT1917) (2.76 g, 73% yield) as a colorless oil which solidified upon standing.

Workup

  1. stirringAfter stirring for 20 hr
  2. extractionextracted with dichloromethane (3×50 ml)
  3. washThe combined organic layers were washed with water (40 ml), with saturated aqueous sodium chloride solution (20 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7b4b3c022d694da6855a0ff1fbb92d3d
Source dataset
uspto-grants-1997_09
Patent number
US05670506

Reaction notes

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