2,4-Dichlorobenzylamine → HCID 58168975, compound

HRID 38764

Reaction equation

HRID 38764 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][N:3]=1.[Cl:16][C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20].O1CCOCC1>C(OCC)(=O)C>[Cl:16][C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[CH2:19][NH:20][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14852,4-DichlorobenzylamineHCID 312751,4-DioxaneHCID 3696469Methyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate

Product 1

HCID 58168975HCID 58168975, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate (0.30 g), 2,4-dichlorobenzyl amine (818 μL), and 1,4-dioxane (3 mL) was stirred at room temperature for 21 hours. To the reaction liquid was added ethyl acetate (30 mL), washed with saturated brine (10 mL), and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain methyl 2-(2,4-dichlorobenzylamino)-4-(trifluoromethyl)pyrimidine-5-carboxylate (446 mg) as a colorless solid.

Workup

  1. customTo the reaction liquid
  2. washwashed with saturated brine (10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-edede3df92e04fa488b7f19f041fa29e
Source dataset
uspto-grants-2013_09
Patent number
US08524727B2

Linked notes

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