Triethylamine → Ethyl 2-(4,6-dimethyl-5-nitropyrimidine-2-ylamino)acetate

HRID 1749265Notes

Reaction equation

HRID 1749265 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1.Cl.[CH2:14]([O:16][C:17](=[O:20])[CH2:18][NH2:19])[CH3:15].C(N(CC)CC)C>C(O)C>[CH3:12][C:4]1[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[N:7]=[C:2]([NH:19][CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:20])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 593361732-Chloro-4,6-dimethyl-5-nitropyrimidine

Product 1

HCID 25120135Ethyl 2-(4,6-dimethyl-5-nitropyrimidine-2-ylamino)acetateYield 87.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Compound 2 (69 mg), glycine ethyl ester hydrochloride (102 mg) and triethylamine (103 μL) in ethanol was stirred for 3 hours under reflux. After the reaction was completed, the mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to give 82 mg (86% yield) of the desired product as a pale yellow amorphous.

Workup

  1. temperatureunder reflux
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-6a7fc63d42c64751b27451d8baeb5501
Source dataset
uspto-grants-2015_10
Patent number
US09156817B2

Reaction notes

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