1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion Chemical Properties

Melting point:

>360 °C(Solv: water (7732-18-5))

Density 

1.516±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder to crystal

pka

11.32±0.20(Predicted)

color 

White to Light yellow to Light orange

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933.59.8000

1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion Usage And Synthesis

Uses

1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion is used for the preparation of pyrazolopyrimidine derivatives or analogs thereof as CCR4 function modulators.

Synthesis

General procedure for the synthesis of 1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione from (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione: (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione (1 g, 4.4 mmol) was dissolved in freshly prepared glacial acetic acid (50 mL) and stirred to form a slurry. Under stirring, zinc powder (stabilized, 1g per batch, 2g total) was added in two batches with an interval of 1 hour. The reaction mixture was stirred overnight and the color of the slurry was observed to change gradually from yellow to light yellow to off-white. After completion of the reaction, the mixture was filtered and the filtrate was concentrated under vacuum to obtain a brown slurry. The product was separated from the brown slurry by ethanol precipitation to give a white solid (0.6 g, 89.8% yield). The spectral data of the product were consistent with those reported in the literature.1H NMR (400 MHz, DMSO-d6): δ 5.82-5.83 (t, 1H, J=2.28 Hz), 7.12-7.13 (t, 1H, J=2.72 Hz, J=2.96 Hz), 10.57 (s, 1H), 10.74 (s, 1H), 11.82 (s. 1H).13C NMR (400 MHz, DMSO-d6): δ 96.5, 110.9, 127.4, 135.1, 152.0, 156.3.

References

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4354 - 4363
[2] Patent: US2016/257696, 2016, A1. Location in patent: Paragraph 0068
[3] Patent: WO2009/62258, 2009, A1. Location in patent: Page/Page column 98
[4] ChemMedChem, 2018, vol. 13, # 2, p. 178 - 185

1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion(65996-50-1)Related Product Information

• METHYL 1H-PYRROLO[3,2-B]PYRIDINE-5-CARBOXYLATE
• 1H-Pyrrolo[3,2-b]pyridine-3-aceticacid(8CI,9CI)
• 1H-Pyrido[2,3-b][1,4]oxazin-2(3H)-one(9CI)
• 1H-Pyrrolo[3,2-c]pyridine-2-carboxylic acid, Methyl ester
• 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, methyl ester
• METHYL 1H-PYRROLO[3,2-B]PYRIDINE-2-CARBOXYLATE
• 1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid
• 1H-Pyrrolo[3,2-c]pyridine-3-ethanamine
• (1H-Pyrrolo[2,3-c]pyridin-3-yl)MethanaMine
• methyl 1H-pyrrolo[3,2-b]pyridine-3-carboxylate
• 2-b]pyridin-3-aMine dihydrochloride
• 3-Cyano-4-azaindole
• Methyl 6-azaindole-3-carboxylate
• 1H-PYRROLO[3,2-B]PYRIDINE-2-CARBOXYLIC ACID
• 1H-PYRROLO[3,2-B]PYRIDINE-2-CARBALDEHYDE
• 1H-PYRAZOLO[3,4-B]PYRAZIN-3-AMINE
• 1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion
• 3-[2-[4-(2-METHOXYPHENYL)PIPERAZIN-1-YL] ETHYL]PYRIMIDO[5,4-B] INDOLE-2,4-DIONE