2-Chloropyrimidine → HCID 86669123, compound

HRID 2400335Notes

Reaction equation

HRID 2400335 reaction equation
[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)(=[O:5])=[O:4].[Cl:12][C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1>CCOCC.CCOC(C)=O>[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:15]1[CH:16]=[CH:17][N:18]=[C:13]([Cl:12])[N:14]=1)(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 744042-ChloropyrimidineHCID 395751N,N-Dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 86669123HCID 86669123, compoundYield 4.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N-BuLi [2.5M in hexane] (4 ml, 10 mmol) added at −78° C. to a solution of N,N-dimethyl imidazole-1-sulphonamide (1.75 g, 10 mmol) in dry ether (60 ml), stirred 1 hour, anion transferred to a suspension of 2-chloropyrimidine (1.48 g, 10 mmol) in ether (80 ml) keeping the temperature -30° C., temperature brought to 0° C. and held for 30 min. Reaction quenched with AcOH (0.64 ml) and water (0.1 ml), to the reaction was added THF (2 ml) then DDQ (2.27 g) in THF (10 ml) and stirred 0/N. Reaction diluted with EtOAc, solid filtered off and filtrate washed with water (3×) then ice cold 0.5% NaOH, organic layer dried over MgSO4, filtered and concentrated under reduced pressure, residue was purified by column chromatography to give the product (130 mg).

Workup

  1. customthe temperature -30° C., temperature
  2. custombrought to 0° C.
  3. waitheld for 30 min
  4. customReaction
  5. customquenched with AcOH (0.64 ml) and water (0.1 ml), to the reaction
  6. additionwas added THF (2 ml)
  7. stirringDDQ (2.27 g) in THF (10 ml) and stirred 0/N
  8. customReaction
  9. filtrationfiltered off
  10. washfiltrate washed with water (3×)
  11. dry with materialice cold 0.5% NaOH, organic layer dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure, residue
  14. customwas purified by column chromatography

Sources & evidence

ORD record
ord-edc1052577f94ac1973ede539e80c6f1
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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