Ethyl Acetate → 4-(Propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxylic acid ethyl ester

HRID 2284633Notes

Reaction equation

HRID 2284633 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:14][CH2:15][CH2:16][CH3:17])=[N:8][C:9](SC)=[N:10][CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])O.[Na+].C(O[CH2:27][CH3:28])(=O)C>CN1CCCC1=O.ClC1C=CC=C(C(OO)=O)C=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:14][CH2:15][CH2:16][CH3:17])=[N:8][C:9]([NH:14][CH2:15][CH2:16][C:28]2[CH:27]=[CH:9][N:8]=[CH:7][CH:6]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 105629752-Methylthio-4-propylamino-5-pyrimidine carboxylic acid ethyl ester

Product 1

HCID 900517144-(Propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 70297m-Chloroperbenzoic acidSolvent2×

Procedure

To a solution of 2-(methylthio)-4-(propylamino)pyrimidine-5-carboxylic acid ethyl ester (A1, 9.0 g) in N-methylpyrrolidone (88 mL), meta-chloroperbenzoic acid (70 to 75% wt, 10.8 g) was added portionwise under ice cooling, and the mixture was stirred at room temperature for 45 minutes. To the reaction mixture, meta-chloroperbenzoic acid (70 to 75% wt, 2.5 g) was added at room temperature, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To a solution of the obtained residue in N-methylpyrrolidone (35 mL), N,N-diisopropylethylamine (11.9 mL) and 4-(2-aminoethyl)pyridine (6.3 mL) were added at room temperature, and the mixture was stirred at 100° C. for 4 hours. The reaction mixture was cooled to room temperature, and then poured into water (400 mL). The solid matter was taken by filtration, washed with water, and then dried under reduced pressure to obtain 4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxylic acid ethyl ester (A2, 9.2 g) as yellow solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 3 hours
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionTo a solution of the obtained residue in N-methylpyrrolidone (35 mL), N,N-diisopropylethylamine (11.9 mL) and 4-(2-aminoethyl)pyridine (6.3 mL) were added at room temperature
  7. stirringthe mixture was stirred at 100° C. for 4 hours
  8. temperatureThe reaction mixture was cooled to room temperature
  9. additionpoured into water (400 mL)
  10. filtrationThe solid matter was taken by filtration
  11. washwashed with water
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-468b9ca9b24640f6937982ba68ecf979
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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