Acetamidine monohydrochloride → Ethyl-2-methyl-4-(2-bromophenyl)-pyrimidine-5-carboxylate

HRID 650621Notes

Reaction equation

HRID 650621 reaction equation
C([O-])C.[Na+].Cl.[C:6]([NH2:9])(=[NH:8])[CH3:7].[CH2:10]([O:12][C:13](=[O:28])[C:14]([C:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Br:26])=[CH:15]N(C)C)[CH3:11]>C(O)C>[CH2:10]([O:12][C:13]([C:14]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Br:26])=[N:8][C:6]([CH3:7])=[N:9][CH:15]=1)=[O:28])[CH3:11]

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxideHCID 541240112-(2-Bromo-benzoyl)-3-dimethylamino-acrylic acid ethyl ester

Product 1

HCID 22831713Ethyl-2-methyl-4-(2-bromophenyl)-pyrimidine-5-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a fresh prepared solution of sodiumethanolate (prepared from 0.77 g (33.7 mmol) Na in 100 ml Ethanol) 3.18 g (33.7 mmol) acetamidinhydrochloride was added. After 10 Min. a solution of 10.0 g (30.6 mmol) 2-(2-bromo-benzoyl)-3-dimethylamino-acrylic acid ethyl ester in 120 ml ethanol was added and the reaction mixture heated for 16 hrs. at 80°. The solvent was evaporated, the residue distributed between 100 ml H2O and 100 ml CH2Cl2. The aqueous phase was extracted twice with 100 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtrated and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 40:1) to give 8.3 g (84%) 4-(2-bromo-phenyl)-2-methyl-pyrimidine-5-carboxylic acid ethyl ester as a pale brown oil.

Workup

  1. temperaturethe reaction mixture heated for 16 hrs
  2. customat 80°
  3. customThe solvent was evaporated
  4. extractionThe aqueous phase was extracted twice with 100 ml CH2Cl2
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltrated
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 40:1)

Sources & evidence

ORD record
ord-77e26a486be34c55a932310aac681e7c
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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