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ChemicalBook CAS DataBase List Propylthiouracil

Propylthiouracil synthesis

2synthesis methods
Propylthiouracil, 6-propyl-2-thio-2,4-(1H,3H)-pyrimidindione (25.2.2), is synthesized by condensating ethyl butyroacetate with thiourea in the presence of sodium ethoxide.

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Yield:51-52-5 78%

Reaction Conditions:

with potassium carbonate in water at 70 - 105; for 3 h;

Steps:

A
3-Oxohexanoic acid methyl ester (1) (2.95 ml_, 20.81 mmol) and K2CO3 (2.819 g, 20,39 mmol) were added to a solution of thiourea (1.044 g, 13.73 mmol) in water (1.8 ml_) at 700C. The obtained mixture was stirred at 1050C for 3 hours, cooled to room temperature and diluted with water (7,5 mi_). Thereafter, concentrated aqueous HCI solution (6.75 ml_) was added carefully. The resulting precipitate was collected by filtration, washed with water and dried, giving compound 2 as a white-yellow solid. Yield 1.815 g, 78%. MW 170.23. LCMS tR (min): 1.17. MS (APCI+), m/z 171.12 [M-t-hTf.

References:

PROGENICS PHARMACEUTICALS, INC.;HAN, Amy, Qi;WANG, Eric;GAUSS, Carla;XIE, Walter;COBURN, Glen;DEMUYS, Jean-Marc WO2010/118367, 2010, A2 Location in patent:Page/Page column 51

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