1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione Chemical Properties

Melting point:

>300 °C

Density 

1.517±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

10.40±0.20(Predicted)

Appearance

White to off-white Solid

InChI

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

InChIKey

QAFVXBQPQCSSLI-UHFFFAOYSA-N

SMILES

C1(=O)NC(=O)C2SC=CC=2N1

CAS DataBase Reference

16233-51-5

Safety Information

Risk Statements 

20/21/22

Safety Statements 

24/25-36/37

HS Code 

29335990

1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione Usage And Synthesis

Chemical Properties

Grey solid

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, PKD (serine/threonine kinases) as well as take part in the synthesis of antagonists of the humane adenosine A2B receptor.

Synthesis

The general procedure for the synthesis of thieno[3,2-d]pyrimidine-2,4-dione from methyl 3-amino-2-thiophenecarboxylate was as follows: to a mixed solution containing methyl 3-amino-2-thiophenecarboxylate (101) (100.0 g, 636.9 mmol, 1.0 eq.), acetic acid (705 mL), and water (600 mL) was added slowly over a period of 1 h. To a mixture containing methyl 3-aminothiophene-2-carboxylate (101) ( 154.8 g, 1.91 mol, 3.0 eq.) of an aqueous solution (326 mL). The reaction mixture was stirred at room temperature for 20 hours before being filtered and the filter cake was washed with deionized water (500 mL). The resulting solid was transferred to an appropriately sized reactor, 2M aqueous sodium hydroxide solution (1.65 L) was added and the slurry was stirred for 2 h. The formation of the target product, thieno[3,2-d]pyrimidine-2,4-dione, was confirmed by LCMS. Subsequently, the reaction mixture was cooled to 10 °C and the pH was adjusted to 5.0-6.0 by slow addition of 3M aqueous hydrochloric acid (1.29 L). The slurry was filtered, the solids were washed with deionized water (700 mL) and dried in a vacuum oven at 50 °C for 24 h. Compound 102 (100 g, 94% yield) was obtained as an off-white solid. lCMS (m/z): 169.1 [ M + H]+. 1H NMR (400MHz, DMSO-d6): δ 6.92 (d, J=5.2Hz, 1H), 8.04 (d, J=5.2Hz, 1H), 11.14 (s, 1H), 11.51 (s, 1H).

References

[1] Patent: WO2018/85342, 2018, A1. Location in patent: Page/Page column 25; 30
[2] Patent: WO2011/49332, 2011, A2. Location in patent: Page/Page column 16
[3] Patent: US2012/277424, 2012, A1. Location in patent: Page/Page column 7
[4] Journal of Chemical Research, Miniprint, 1993, # 2, p. 548 - 575
[5] Patent: CN103980287, 2016, B. Location in patent: Paragraph 0117; 0118; 0119

1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione(16233-51-5)Related Product Information

• THIENO[3,2-D]PYRIMIDIN-4(3H)-ONE
• Thieno[2,3-b]pyridine (8CI,9CI)
• THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID
• thieno[3,2-c]pyridine
• Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde
• tert-butyl thiazol-5-ylcarbamate
• Thieno[2,3-b]pyridine-5-carboxylic acid
• Thiazole-4-carboxaldehyde
• Methyl 2-Thiazolecarboxylate
• Thiazole-5-carboxylic acid
• THIENO[2,3-B]PYRIDINE-2-CARBALDEHYDE
• Thieno[3,2-b]pyridine-6-carboxylic acid
• Thieno[3,2-b]thiophene
• METHYL THIOPHENE-2-CARBOXYLATE
• methyl thiazolo[4,5-b]pyridine-6-carboxylate
• THIENO(3 2-B)PYRIDIN-7-OL
• Thieno[2,3-c]pyridine-6(5H)-acetic acid, -(2-chlorophenyl)-4,7-dihydro-, methyl ester
• Thieno[3,2-b]pyridine, 3-amino- (6CI)