Pyrimidine, 2,4-dichloro-5-methyl- → HCID 59336170, compound

HRID 2359462Notes

Reaction equation

HRID 2359462 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[Cl:9][C:10]1[N:15]=[C:14](Cl)[C:13]([CH3:17])=[CH:12][N:11]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:9][C:10]1[N:15]=[C:14]([NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])[C:13]([CH3:17])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 59336170HCID 59336170, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

Glycine ethyl ester hydrochloride (157 mg) was added to a solution of 2,4-dichloro-5-methylpyrimidine (184 mg) and diisopropylethylamine (486 μL) in acetonitrile (3 mL) while the solution was cooled with ice. The mixture was stirred at 40° C. overnight. Subsequently, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (ethyl acetate: hexane=1:3 to 1:1) to give 205 mg (81% yield) of the desired product as a white amorphous.

Workup

  1. temperaturewas cooled with ice
  2. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate: hexane=1:3 to 1:1)

Sources & evidence

ORD record
ord-a6fe18c16daf4f359dc980cacf25149e
Source dataset
uspto-grants-2014_04
Patent number
US08685989B2

Reaction notes

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