Hydrochloric Acid → 2-Methylthio-4-propylamino-5-pyrimidine carboxylic acid ethyl ester

HRID 2284632Notes

Reaction equation

HRID 2284632 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].Cl.C(O[CH2:20][CH3:21])(=O)C.[CH2:22]([N:24](CC)CC)C>O1CCCC1.C(N)CC>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:24][CH2:22][CH2:20][CH3:21])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 105629752-Methylthio-4-propylamino-5-pyrimidine carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 7852PropylamineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester (11.6 g) in tetrahydrofuran (100 mL), triethylamine (8.4 mL) and propylamine (5.1 mL) were added under ice cooling, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, 1.0 mol/L aqueous hydrochloric acid and ethyl acetate were added. The organic layer was separated, washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain oily 2-(methylthio)-4-(propylamino)pyrimidine-5-carboxylic acid ethyl ester (A1, 11.7 g).

Workup

  1. customThe organic layer was separated
  2. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0bda7185606944579ddb9ddcf21f9ef3
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

Loading…