Water → HCID 57592518, compound

HRID 1784371Notes

Reaction equation

HRID 1784371 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[N:6]=1.C([Li])CCC.[Cl:13][C:14]1[N:19]=[C:18](Cl)[CH:17]=[CH:16][N:15]=1.O.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[OH-].[Na+]>C(OCC)C.C1COCC1>[Br:7][C:5]1[N:6]=[C:2]([C:16]2[CH:17]=[CH:18][N:19]=[C:14]([Cl:13])[N:15]=2)[S:3][CH:4]=1

Participants

9

Reactant 6

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14798Sodium HydroxideHCID 775312,4-DichloropyrimidineHCID 27632972,4-Dibromo-1,3-thiazoleHCID 178418339Butyllithium

Product 1

HCID 57592518HCID 57592518, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of 2,4-dibromothiazole (24)(0.73 g, 3.0 mmol) in anhydrous diethylether (7 ml) was added n-butyllithium (2.5M in hexane, 1.5 ml, 3.28 mmol) in a dropwise fashion via syringe. The yellow solution was stirred at −78° C. for 15 minutes before the addition of a suspension of 2-chloropyrimidine (20)(2.73 mmol, 0.313 g) in anhydrous diethylether (8 ml). The mixture was allowed to warm to room temperature and maintained like this, with stirring for 16 hours. The mixture was quenched carefully by dropwise addition of water (0.061 ml, 3.41 mmol) in THF (0.7 ml) and then DDQ (0.681 g, 3.0 mmol) added to effect aromatization. The mixture was cooled to 0° C. and 3M NaOH (aq) (2.28 ml, 6.83 mmol) added which caused a sticky solid to adhere to bottom of the reaction vessel. The solvents were collected, dried (MgSO4), filtered and concentrated in vacuo to give the title compound (0.58 g, 69.8%) in suitably clean form to be used without further purification. m/z (LC-MS, ESP): 327 [M+H]+, R/T=3.73 mins.

Workup

  1. temperaturemaintained like this,
  2. temperatureThe mixture was cooled to 0° C.
  3. customThe solvents were collected
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6483d471942f45de88adb81834180996
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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