Ethylamine → Ethyl 4-(ethylamino)-2-(methylthio)pyrimidine-5-carboxylate

HRID 871838Notes

Reaction equation

HRID 871838 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[CH2:15]([N:17](CC)CC)[CH3:16].C(N)C>C1COCC1.O>[CH2:15]([NH:17][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1)[CH3:16]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 8471TriethylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 10514260Ethyl 4-(ethylamino)-2-(methylthio)pyrimidine-5-carboxylateYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15.0 g (64.0 mmol) of ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate and 195 mL (1.39 mol) of triethylamine in 226 mL of THF are added 14.6 mL of aqueous 70% ethylamine solution. The mixture is stirred at room temperature for 2 hours. After diluting in water, the resulting mixture is extracted with ethyl acetate and the organic phase is dried over MgSO4. The product is purified by chromatography on silica gel, eluting with a cyclohexane/EtOAc mixture (8/15). 13.7 g of expected product are obtained in the form of a colourless oil. Yield=89%.

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. dry with materialthe organic phase is dried over MgSO4
  3. customThe product is purified by chromatography on silica gel
  4. washeluting with a cyclohexane/EtOAc mixture (8/15)

Sources & evidence

ORD record
ord-ea376fc1bf57453c88c7af3efdd87327
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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