4-CHLORO-2-METHYL-THIENO[2,3-D]PYRIMIDINE Chemical Properties

Melting point:

90 - 92°C

Boiling point:

208.1±22.0 °C(Predicted)

Density 

1.445±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

0.87±0.40(Predicted)

color 

Beige

InChI

InChI=1S/C7H5ClN2S/c1-4-9-6(8)5-2-3-11-7(5)10-4/h2-3H,1H3

InChIKey

VYUDXHRVZLZWMP-UHFFFAOYSA-N

SMILES

C1(C)=NC(Cl)=C2C=CSC2=N1

Safety Information

HS Code 

2934999090

4-CHLORO-2-METHYL-THIENO[2,3-D]PYRIMIDINE Usage And Synthesis

Uses

4-Chloro-2-methylthieno[2,3-D]pyrimidine can be used as a pharmaceutical synthesis intermediate. It can be prepared from methyl 2-aminothiophene-3-carboxylic acid as a reactant, and then further reacted with phosphorus oxychloride to obtain the intermediate 2-methyl-3H-thieno[2,3-d]pyrimidine-4-one.

Synthesis

The general procedure for the synthesis of 4-chloro-2-methylthieno[2,3-D]pyrimidines from 4-hydroxy-2-methylthieno[2,3-D]pyrimidines was as follows: a few drops of pyridine were added to a solution of 2-methylthieno[2,3-d]pyrimidin-4(3H)-one (300 mg, 1.80 mmol) in phosphorus oxychloride (POCl3, 5.0 mL). The reaction mixture was heated to reflux for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice water. Subsequently, saturated sodium carbonate (Na2CO3) solution was added to neutralize the excess trichlorophosphate. The aqueous phase was extracted with ethyl acetate (EtOAc) and the organic phase was combined. The organic phase was washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with the eluent of petroleum ether/ethyl acetate (8:2, v/v) to afford the target compound 4-chloro-2-methylthieno[2,3-D]pyrimidine in 61% yield. The product was a yellow solid with a melting point of 93 °C. Nuclear magnetic resonance hydrogen spectrum (1H NMR, 200 MHz, CDCl3) δ= 7.48 (d, J = 6.0 Hz, 1H), 7.35 (d, J = 6.0 Hz, 1H), 2.79 (s, 3H). Nuclear magnetic resonance carbon spectrum (13C NMR, 50 MHz, CDCl3) δ= 169.2, 163.0, 154.4, 126.8, 126.6, 119.5, 25.5. liquid chromatography-mass spectrometry (LC-MS, ESI, 35 eV): retention time (tR) = 1.84 min, mass-to-charge ratio (m/z) = 185 [M + H]+ The results are summarized in the following table.

References

[1] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 68 - 86

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