Aniline → Ethyl 2-(methylthio)-4-(phenylamino)pyrimidine-5-carboxylate

HRID 871883Notes

Reaction equation

HRID 871883 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.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C1COCC1>[CH3:14][S:13][C:4]1[N:3]=[C:2]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 295672Ethyl 2-(methylthio)-4-(phenylamino)pyrimidine-5-carboxylateYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.0 g (21.49 mmol) of ethyl 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate and 4.9 mL (53.72 mmol) of aniline in 75 mL of THF are added 7.49 mL (53.72 mmol) of triethylamine. The mixture is stirred at room temperature overnight. After evaporating off the THF, aqueous 1N HCl solution is added and the mixture is extracted with ethyl acetate. The organic phase is washed with saturated aqueous NaHCO3 solution and then with NaCl solution. The organic phase is dried over MgSO4. After filtering, the filtrate is concentrated to give 3.99 g of the expected product in the form of a beige-coloured solid, which is used as obtained in the following step. Yield=64%.

Workup

  1. customAfter evaporating off the THF, aqueous 1N HCl solution
  2. additionis added
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic phase is washed with saturated aqueous NaHCO3 solution
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationAfter filtering
  7. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-dad508be5f3649d5b1b2e48d2048aa18
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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