ETHYL 4-CHLORO-5-METHYLTHIENO[2,3-D]PYRIMIDINE-6-CARBOXYLATE Chemical Properties

Melting point:

114-115 °C(Solv: chloroform (67-66-3); hexane (110-54-3))

Boiling point:

374.4±37.0 °C(Predicted)

Density 

1.409

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.01±0.40(Predicted)

Safety Information

HS Code 

2933599590

ETHYL 4-CHLORO-5-METHYLTHIENO[2,3-D]PYRIMIDINE-6-CARBOXYLATE Usage And Synthesis

Synthesis

Ethyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-D]-pyrimidine-6-carboxylate (425 mg, 1.783 mmol) was used as a starting material, and after dissolution in toluene (8 mL), N,N-diisopropylethylamine (DIPEA, 248 μL, 1.426 mmol, 0.8 eq.) and phosphorus oxychloride (POCl3, 199 μ L, 2.14 mmol, 1.2 equiv). The reaction mixture was heated to reflux in an oil bath at 120-125°C for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently slowly poured into a mixed system of ice-cooled saturated aqueous sodium bicarbonate (20 mL) and ethyl acetate (EtOAc, 50 mL) with rapid stirring to thoroughly quench the excess of phosphorous trichloride. The organic and aqueous phases were separated and the organic phase was washed once more with saturated aqueous sodium bicarbonate (20 mL). The organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to afford ethyl 4-chloro-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (25B) as a yellow solid (432 mg, 94% yield).

References

[1] Patent: WO2005/42537, 2005, A1. Location in patent: Page/Page column 57
[2] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 148 - 160
[3] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 9, p. 1663 - 1669
[4] Pharmazie, 1993, vol. 48, # 3, p. 192 - 194
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1985, vol. 21, # 7, p. 767 - 770

ETHYL 4-CHLORO-5-METHYLTHIENO[2,3-D]PYRIMIDINE-6-CARBOXYLATE(101667-98-5)Related Product Information

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