Diisopropylamine → HCID 53772531, compound

HRID 846537Notes

Reaction equation

HRID 846537 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].[CH3:26][O:27][C:28]1[CH:33]=[C:32]([O:34][CH3:35])[N:31]=[C:30](S(C)(=O)=O)[N:29]=1>O1CCCC1>[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([C:30]1[N:31]=[C:32]([O:34][CH3:35])[CH:33]=[C:28]([O:27][CH3:26])[N:29]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 96528Ethyl (2-methylphenyl)acetateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 53772531HCID 53772531, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-75 °C

Procedure

n-Butyllithium (10 ml of 2N solution in pentane) was added dropwise to a stirred solution of di-isopropylamine (2.0 g) in dry tetrahydrofuran (40 ml) under nitrogen at -10° C. After stirring at this temperature for 15 minutes, the solution was cooled to -75° C., and a solution of ethyl (2-methylphenyl)acetate (3.56 g) in tetrahydrofuran (20 ml) was added dropwise. After stirring at -75° C. for one hour, 4,6-dimethoxy-2-(methylsulphonyl)pyrimidine (4.36 g) was added in one portion, and the resulting suspension was allowed to warm slowly to room temperature before stirring overnight. The reaction mixture was then poured onto water (400 ml) and the resulting oil was extracted into ether (2×150 ml). The combined extracts were washed with saturated sodium chloride solution, dried over magnesium sulphate and evaporated to give a yellow oil which was purified by chromatography to give 3.8 g of the desired product as a colourless oil.

Workup

  1. stirringAfter stirring at -75° C. for one hour
  2. temperatureto warm slowly to room temperature
  3. stirringbefore stirring overnight
  4. additionThe reaction mixture was then poured onto water (400 ml)
  5. extractionthe resulting oil was extracted into ether (2×150 ml)
  6. washThe combined extracts were washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customto give a yellow oil which
  10. customwas purified by chromatography

Sources & evidence

ORD record
ord-992da6394fc242428a56b9f58eb0d7b4
Source dataset
uspto-grants-1992_08
Patent number
US05137564

Reaction notes

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