2,4-Dihydroxythieno[2,3-d]pyrimidine Chemical Properties

Melting point:

322 °C

Density 

1.517±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

10.40±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C6H4N2O2S/c9-4-3-1-2-11-5(3)8-6(10)7-4/h1-2H,(H2,7,8,9,10)

InChIKey

JGOOQALRLGHKIY-UHFFFAOYSA-N

SMILES

C1(=O)NC(=O)C2C=CSC=2N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

2,4-Dihydroxythieno[2,3-d]pyrimidine Usage And Synthesis

Uses

1H-Thieno[3,4-d]pyrimidine-2,4-dione is an analog of thieno[3,4-d]pyrimidine and can serve as an inhibitor of dipeptidyl peptidase IV.

Synthesis

Methyl 2-aminothiophene-3-carboxylate (95 g) and dichloromethane (2.85 L) were added to a 5 L reaction flask fitted with a mechanical stirrer, an internal temperature probe, and a nitrogen bubbler, and the mixture was cooled to -60 °C. Chlorosulfonyl isocyanate (89.81 g) was slowly added while maintaining the internal temperature at -60°C to -55°C. After addition, the reaction mixture was allowed to gradually warm up to room temperature. The reaction was monitored by LC/MS until the feedstock was completely consumed. The reaction mixture was concentrated to dryness under vacuum and the solid residue was transferred to a 5L reaction flask with water (1.8L). The mixture was heated at 75 °C for 1 h and then cooled to 30 °C. Subsequently, 10M NaOH aqueous solution (200mL) was added and the mixture was heated at 85°C for 20 minutes and then cooled to room temperature. The mixture was acidified to pH=1 with concentrated hydrochloric acid and stirred at room temperature for 18 hours, during which time a precipitate formed. The solid was collected by vacuum filtration and the filter cake was washed with water (3 x 300 mL). The solid was dried in a vacuum oven at 55 °C for 24 h to afford thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione as an off-white solid (80.05 g, 78.8% yield).1H NMR (400 MHz, DMSO-d6) δ 7.083 (d, J=5.6 Hz, 1H), δ 7.124 (d, J=5.6 Hz , 1H); LCMS (ESI pos) m/e 169 (M+1).

References

[1] Patent: WO2008/73785, 2008, A2. Location in patent: Page/Page column 169
[2] MedChemComm, 2014, vol. 5, # 12, p. 1821 - 1828

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