Water → 3-(4,6-Dimethoxypyrimidine-2-yl)-2,7-dimethylindole

HRID 916736

Reaction equation

HRID 916736 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][C:12](=O)[CH3:13])[N:4]=1.Cl.[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23]N.C(OCC)(=O)C.O>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2[C:19]3[C:18](=[C:17]([CH3:16])[CH:22]=[CH:21][CH:20]=3)[NH:23][C:12]=2[CH3:13])[N:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 112640521-(4,6-Dimethoxypyrimidin-2-yl)propan-2-one

Product 1

HCID 129793703-(4,6-Dimethoxypyrimidine-2-yl)-2,7-dimethylindoleYield 34.2%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

In 20 ml of toluene were dissolved 0.77 g (3.9 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone and 0.69 g (4.3 m moles) of 2-methylphenylhydrazine hydrochloride. Thereto was added 0.64 g (4.7 m moles) of zinc chloride, followed by refluxing for 2 hours. The reaction mixture was allowed to cool, and then ethyl acetate and water were added to dissolve the whole reaction mixture. The oily layer was washed with water, separated and dried over Glauber's salt. The resulting oily layer was concentrated under reduced pressure using a rotary evaporator, to obtain an orange solid. The solid was treated with ethyl acetate/n-hexane to obtain 0.38 g (1.34 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-2,7-dimethylindole. Yield: 34% Melting point: 145 to 147° C.

Workup

  1. temperatureby refluxing for 2 hours
  2. temperatureto cool
  3. dissolutionto dissolve
  4. customthe whole reaction mixture
  5. washThe oily layer was washed with water
  6. customseparated
  7. dry with materialdried over Glauber's salt
  8. concentrationThe resulting oily layer was concentrated under reduced pressure
  9. customa rotary evaporator
  10. customto obtain an orange solid

Sources & evidence

ORD record
ord-140b0b070ab54e4383209e8b9583c446
Source dataset
uspto-grants-2007_09
Patent number
US07271263B2

Linked notes

Loading…