Water → HCID 68704968, compound

HRID 61983Notes

Reaction equation

HRID 61983 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14](=O)[CH:15]=[CH:16]N(C)C)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9][CH3:10].[F:21][C:22]([F:33])([F:32])[C:23]1[N:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](=[NH:27])[NH2:26].CC(C)([O-])C.[K+].O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14]2[CH:15]=[CH:16][N:26]=[C:25]([C:24]3[C:23]([C:22]([F:32])([F:21])[F:33])=[N:31][CH:30]=[CH:29][CH:28]=3)[N:27]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 670368751-(3,4-Dimethoxy-5-nitrophenyl)-3-(dimethylamino)prop-2-en-1-oneHCID 67359629HCID 67359629, compound

Product 1

HCID 68704968HCID 68704968, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of 1-(3,4-dimethoxy-5-nitro-phenyl)-3-dimethylamino-propen-1-one (0.28 g, 1.0 mmol), 2-(trifluoromethyl)nicotinimidamide (0.283 g, 1.5 mmol) and potassium tert-butoxide (0.17 g, 1.5 mmol) in absolute ethanol (5 mL) was heated to 80° C. in a sealed tube for one hour and then allowed to cool to room temperature. The mixture was poured onto cold water (100 mL) and the resulting precipitate was filtered off, washed with water and dried to give 4-(3,4-dimethoxy-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)pyrimidine, 0.296 g (73%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe resulting precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8e119eca4340435285bb57712532fcc4
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Reaction notes

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