Ethylamine → Ethyl 4-(ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carboxylate

HRID 1893889Notes

Reaction equation

HRID 1893889 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1.[CH2:16]([N:18](CC)CC)[CH3:17].C(N)C>C1COCC1>[CH2:16]([NH:18][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1)[CH3:17]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 8471TriethylamineHCID 22225416Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

Product 1

HCID 57606964Ethyl 4-(ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carboxylateYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate (65 g) in THF (1000 mL) and triethylamine (110 mL, 0.81 mole) was added ethylamine (2.0 M in THF, 0.81 mole) at 0° C. This reaction mixture was stirred at room temperature overnight and then solvents were removed on a rotary evaporator. H2O was added and the mixture extracted with ethyl acetate several times. Solvents from the combined organic layers were removed on a rotary evaporator affording 58 g (86% yield) of ethyl 4-(ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carboxylate. This material was used as such without further purification.

Workup

  1. customsolvents were removed on a rotary evaporator
  2. additionH2O was added
  3. extractionthe mixture extracted with ethyl acetate several times
  4. customSolvents from the combined organic layers were removed on a rotary evaporator

Sources & evidence

ORD record
ord-5512adfad8d548e7a79676ee87192e65
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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