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

HRID 2112239Notes

Reaction equation

HRID 2112239 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.[CH3:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24]N.C1(C)C=CC=CC=1.O>[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C>[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:19](=[C:18]([CH2:17][O:16][CH3:15])[CH:23]=[CH:22][CH:21]=3)[NH:24][C:12]=2[CH3:13])[N:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 112640521-(4,6-Dimethoxypyrimidin-2-yl)propan-2-oneHCID 129793652-Methoxymethylphenylhydrazine

Product 1

HCID 115732153-(4,6-Dimethoxypyrimidine-2-yl)-2-methyl-7-metoxymethylindoleYield 46.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Into a reactor were fed 6.2 g (31.6 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone, 4.8 g (31.5 m moles) of 2-methoxymethylphenylhydrazine, 4.76 g (34.9 m moles) of zinc chloride and 60 ml of toluene. Refluxing was made for 2 hours with heating. After the completion of the reaction, the reaction mixture was cooled to room temperature. Water and ethyl acetate were added and phase separation was made. The ethyl acetate layer was concentrated. The resulting crystals were washed with diisopropyl ether to obtain 4.57 g (14.6 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methyl-7-metoxymethylindole. Yield: 46%

Workup

  1. customInto a reactor were fed
  2. temperatureRefluxing
  3. temperaturewith heating
  4. customAfter the completion of the reaction
  5. customphase separation
  6. concentrationThe ethyl acetate layer was concentrated
  7. washThe resulting crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-7f22a1c8eab446239044b236fa08d224
Source dataset
uspto-grants-2009_04
Patent number
US07521555B2

Reaction notes

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