Thieno[2,3-d]pyrimidin-4(3H)one Chemical Properties

Melting point:

262-265°C

Boiling point:

391.1±15.0 °C(Predicted)

Density 

1.63±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in DMSO, Methanol

form 

powder to crystal

pka

10.84±0.20(Predicted)

color 

Light yellow to Brown

InChI

InChI=1S/C6H4N2OS/c9-5-4-1-2-10-6(4)8-3-7-5/h1-3H,(H,7,8,9)

InChIKey

JEDVKUHCDPPWNR-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

14080-50-3

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2934999090

Thieno[2,3-d]pyrimidin-4(3H)one Usage And Synthesis

Chemical Properties

Brown Solid

Uses

4-Hydroxythieno[2,3-d]pyrimidine (cas# 14080-50-3) is a compound useful in organic synthesis.

Synthesis

Thieno[2,3-d]pyrimidin-4(3H)-one was synthesized from methyl 2-aminothiophene-3-carboxylate (3.0 g, 19.1 mmol) and formamide (95 ml) by heating and reacting at 190 °C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and poured into water. The precipitate was collected by filtration, washed with water and dried. The crude product was purified by silica gel column chromatography (eluent: CH2Cl2/MeOH = 50:1) to afford the target compound thieno[2,3-d]pyrimidin-4(3H)-one as a white solid (1.93 g, 66% yield). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO, 25 °C) and HRMS: 1H NMR δ= 12.49 (s, 1H, NH), 8.13 (s, 1H, CH), 7.58 (d, J = 5.8 Hz, 1H, CH), 7.39 (d, J = 5.8 Hz, 1H, CH) ppm; HRMS (calculated) C6H5N2OS: 153.01226, measured value: 153.01155).

References

[1] Patent: US2012/46278, 2012, A1. Location in patent: Page/Page column 81
[2] Patent: US2013/190297, 2013, A1. Location in patent: Paragraph 1205; 1206; 1207
[3] Patent: US2014/88088, 2014, A1. Location in patent: Paragraph 1220-1222
[4] Patent: CN107573386, 2018, A. Location in patent: Paragraph 0048-0050
[5] Tetrahedron, 2012, vol. 68, # 45, p. 9226 - 9233

Thieno[2,3-d]pyrimidin-4(3H)one(14080-50-3)Related Product Information

• 2,4-Dihydroxythieno[2,3-d]pyrimidine
• THIENO[2,3-B]PYRAZIN-7-AMINE
• Thieno[3,2-d]pyrimidine-4-carboxylic acid
• Thieno[2,3-b]pyridine (8CI,9CI)
• thieno[2,3-b]pyridin-4-ol
• Methyl thieno[2,3-b]pyridine-2-carboxylate
• thieno[2,3-d]thiazol-2-amine
• 5-[(tert-butoxy)carbonyl]-3-Methyl-4H,5H,6H,7H- thieno[3,2-c]pyridine-2-carboxylic acid
• ethyl 3-aMino-6-(trifluoroMethyl)thieno[2,3- b]pyridine-2-carboxylate
• 4-HYDROXYTHIENO[3,2-C]PYRIDINE
• 4-CHLOROTHIENO[2,3-B]PYRIDINE-5-CARBONITRILE
• THIENO[3,2-D]PYRIMIDIN-4(3H)-ONE
• Thiazolo[5,4-c]pyridin-2-amine, 6-methoxy-
• 7-BROMOTHIENO[3,2-D]PYRIMIDIN-4(1H)-ONE
• 2-(TRIFLUOROMETHYL)THIENO[3,2-D]PYRIMIDIN-4-OL
• 1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione
• 5-(4-FLUOROPHENYL)-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE
• 5-thien-2-ylthieno[2,3-d]pyrimidin-4(3H)-one