Diisopropylamine → HCID 22420763, compound

HRID 1440960Notes

Reaction equation

HRID 1440960 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[F:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24](S(C)(=O)=O)[N:23]=1>CCCCCC.O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[F:13][CH:14]([C:24]1[N:25]=[C:26]([O:28][CH3:29])[CH:27]=[C:22]([O:21][CH3:20])[N:23]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 9988Ethyl fluoroacetateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 22420763HCID 22420763, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

Butyllithium (21ml of a 1.6M solution in hexane) was added to di-isopropylamine (4.94ml) in dry tetrahydrofuran (100ml) under nitrogen at a temperature of -78° C., and the mixture was stirred for 30 minutes. A solution of ethyl fluoroacetate (2.51g) in dry tetrahydrofuran (20ml) was then added at a temperature of -60° C., and the mixture was stirred for 1 hour. Hexamethylphosphoric triamide (5.12ml) was added, and the mixture was stirred for a further 10 minutes. Then 4,6-dimethoxy-2methylsulfonylpyrimidine (5.0g) was added portionwise, and the temperature of the reaction mixture rose within 2.5 hours to room temperature. The reaction mixture was washed with saturated ammonium chloride and sodium chloride solution, the aqueous phase was extracted with ethyl acetate, and the combined organic layers were dried over magnesium sulfate and evaporated. The product obtained was chromatographed on silica gel using hexane/ethyl acetate (0-20% ethyl acetate), to give the desired compound as a yellow oil (0.56g), refractive index at 20° C. =1.4829.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. stirringthe mixture was stirred for a further 10 minutes
  3. washThe reaction mixture was washed with saturated ammonium chloride and sodium chloride solution
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. customevaporated
  7. customThe product obtained
  8. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-7fe756af73524598818e2ad6554b1103
Source dataset
uspto-grants-1996_03
Patent number
US05502028

Reaction notes

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