Benzaldehyde → HCID 4549161, compound

HRID 1534304Notes

Reaction equation

HRID 1534304 reaction equation
C(NC(C)C)(C)C.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.[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1.CCCCCC.O>[CH3:22][O:21][C:19]1[CH:20]=[C:15]([O:14][CH3:13])[N:16]=[C:17]([S:23][C:24](=[CH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:25]([O:27][CH3:28])=[O:26])[N:18]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 7912DiisopropylamineHCID 5045179HCID 5045179, compoundHCID 178418339Butyllithium

Product 1

HCID 4549161HCID 4549161, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

2.8 g (28.7 mmol) Diisopropylamine was dissolved in 80 ml tetrahydrofuran under nitrogen and treated with 11.5 ml (28.7 mmol) 2.5M n-butyllithium in hexane at a temperature between -78° and -50° C. The mixture was stirred for 10 minutes and then a solution of 7 g (28.7 mmol) methyl 2-(4,6-dimethoxy-2-pyrimidinylthio)acetate in 80 ml tetrahydrofuran was added to the reaction mixture and the mixture then stirred for 20 minutes. 2.8 g (28.7 mmol) Benzaldehyde was added, dropwise, to the solution. The reaction mixture was slowly allowed to reach room temperature, with stirring, and then stirred for 16 hours. The precipitate was treated with 500 ml 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 20 minutes
  2. customto reach room temperature
  3. stirringwith stirring
  4. stirringstirred for 16 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-719cd55b74534d0a83356adc94a41beb
Source dataset
uspto-grants-1992_02
Patent number
US05089044

Reaction notes

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