4-Dimethylaminoacetophenone → HCID 73320054, compound

HRID 2063610Notes

Reaction equation

HRID 2063610 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([NH:9][NH2:10])[CH:6]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[N:4]=1)[CH3:2].[CH3:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=1)=O>C(O)C>[CH2:1]([C:3]1[N:8]=[C:7]([NH:9][N:10]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=2)[CH3:19])[CH:6]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 750374-DimethylaminoacetophenoneHCID 60209697HCID 60209697, compound

Product 1

HCID 73320054HCID 73320054, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [2-Ethyl-6-(2-methoxy-phenyl)-pyrimidin-4-yl]-hydrazine (100 mg, 0.41 mmol) and 4-dimethylaminoacetophenone (67 mg, 0.41 mmol) in ethanol (1.0 mL) was heated in the microwave (CEM Discover, 150 C, QuickTest method) for 6 hours. An initial purification by Si gel chromatography (2:1 hexanes:ethyl acetate) was followed by a crystallization from ethyl acetate:hexanes to yield 20 mg (13%) of the title compound as a yellow solid. HPLC Purity: 97%.

Workup

  1. customAn initial purification by Si gel chromatography (2:1 hexanes:ethyl acetate)
  2. customwas followed by a crystallization from ethyl acetate

Sources & evidence

ORD record
ord-5e4c89c2f4584b82988c93441e54dd3b
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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