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

HRID 916735

Reaction equation

HRID 916735 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.[C:15]1([NH:21]N)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(OCC)(=O)C.O>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:21][C:12]=2[CH3:13])[N:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7516PhenylhydrazineHCID 8857Ethyl AcetateHCID 112640521-(4,6-Dimethoxypyrimidin-2-yl)propan-2-one

Product 1

HCID 129793683-(4,6-Dimethoxypyrimidine-2-yl)-2-methylindoleYield 62%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

In 10 ml of toluene were dissolved 1.61 g (8.2 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone and 1.08 g (10 m moles) of phenylhydrazine. Thereto was added 1.36 g (10 m moles) of zinc chloride, followed by refluxing for 1 hour. The reaction mixture was allowed to cool, and 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 to obtain an orange solid. The solid was recrystallized from methanol to obtain 1.37 g (5.1 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole. Yield: 62% Melting point: 182 to 184° C.

Workup

  1. temperatureby refluxing for 1 hour
  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. customto obtain an orange solid
  10. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-2feaa5f7a42b4d308b7c72c5fe2b5e84
Source dataset
uspto-grants-2007_09
Patent number
US07271263B2

Linked notes

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