Hydrochloric Acid → Methyl(4-(4-bromobenzylamino)-2,6-dimethylpyrimidin-5-yl)ketone

HRID 129019Notes

Reaction equation

HRID 129019 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]2[C:13]([C:14]([O:16]CC)=[CH2:15])=[C:12]([CH3:19])[N:11]=[C:10]([CH3:20])[N:9]=2)=[CH:4][CH:3]=1.Cl>CC(C)=O>[CH3:15][C:14]([C:13]1[C:8]([NH:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:22][CH:21]=2)=[N:9][C:10]([CH3:20])=[N:11][C:12]=1[CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 107373314-(4-Bromobenzylamino)-2,6-dimethyl-5-(1-ethoxyvinyl)pyrimidine

Product 1

HCID 10688121Methyl(4-(4-bromobenzylamino)-2,6-dimethylpyrimidin-5-yl)ketoneYield 89.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-(4-bromobenzylamino)-2,6-dimethyl-5-(1-ethoxyvinyl)pyrimidine (2.72 g, 7.51 mmol), 1N HCl (8.3 mL), and acetone (8 mL) was heated under reflux for 2.5 h. The acetone was removed under reduced pressure and the aqueous phase was adjusted to pH 4 with 1N KOH. The resultant white precipitate was collected by filtration to give 2.24 g (89%) of product as a white solid. An analytical sample was recrystallized from hexane, mp 78°-80° C.

Workup

  1. temperatureunder reflux for 2.5 h
  2. customThe acetone was removed under reduced pressure
  3. filtrationThe resultant white precipitate was collected by filtration

Sources & evidence

ORD record
ord-a831f563ccab4f2f8b953310d6677e38
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Reaction notes

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