Allyl bromide → HCID 14853367, compound

HRID 326528Notes

Reaction equation

HRID 326528 reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].C([Li])CCC.[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([S:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[N:16]=1.BrCC=C>O1CCCC1.CCCCCC>[CH3:22][O:21][C:19]1[CH:20]=[C:15]([O:14][CH3:13])[N:16]=[C:17]([S:23][CH:24]([CH2:3][CH:1]=[CH2:2])[C:25]([O:27][CH3:28])=[O:26])[N:18]=1

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 7912DiisopropylamineHCID 5045179HCID 5045179, compoundHCID 178418339Butyllithium

Product 1

HCID 14853367HCID 14853367, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

1.22 g (12.2 mmol) Diisopropylamine was dissolved in 10 ml tetrahydrofuran under nitrogen and treated with 7.8 ml (12.2 mmol) 1.6M n-butyllithium in hexane at a temperature between -78° and -50° C. The mixture was stirred for 20 minutes and then a solution of 3 g (12.2 mmol) methyl 2-(4,6-dimethoxy-2-pyrimidinylthio)acetate in 30 ml tetrahydrofuran was added to the reaction mixture and the mixture then stirred for 30 minutes. 1.45 g (12.2 mmol) 3-Bromopropene was added, dropwise, to the solution. The reaction mixture was slowly allowed to reach room temperature, with stirring, and then stirred for 20 hours. The mixture was added to 100 ml ice/water and extracted with ethyl acetate. The ethyl acetate phase, after drying over magnesium sulphate, was evaporated and then purified by medium pressure chromatography using hexane/ethyl acetate as eluent.

Workup

  1. stirringthe mixture then stirred for 30 minutes
  2. customto reach room temperature
  3. stirringwith stirring
  4. stirringstirred for 20 hours
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate phase, after drying over magnesium sulphate
  7. customwas evaporated
  8. custompurified by medium pressure chromatography

Sources & evidence

ORD record
ord-e7fefbd23580456c9369317ed42269e5
Source dataset
uspto-grants-1993_12
Patent number
US05270289

Reaction notes

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