| Identification | Back Directory | [Name]
1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion | [CAS]
65996-50-1 | [Synonyms]
65996-50-1
1,5-dihydro-pyrrolo[3,2-a]pyri
5H-Pyrrolo[3,2-d]pyriMidine-2,4-diol
1-Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione
1,5-DIHYDROPYRROLO[3,2-A]PYRIMIDINE-2,4-DION
1,5-DIHYDRO-PYRROLO[3,2-A]PYRIMIDINE-2,4-DIONE
1,5-DIHYDRO-PYRROLO[3,2-D]PYRIMIDINE-2,4-DIONE
1H,2H,3H,4H,5H-pyrrolo[3,2-d]pyriMidine-2,4-dione
1,5-Dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-dione | [Molecular Formula]
C6H5N3O2 | [MDL Number]
MFCD08059275 | [MOL File]
65996-50-1.mol | [Molecular Weight]
151.12 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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