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| | 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE Basic information |
| Product Name: | 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE | | Synonyms: | 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE;2,4-Dichloropyrrolo[3,2-d]pyrimidine;2,4-Dichloro-5H-pyrrolo[3...;2-d]pyriMidine;4-dichloro-5H-pyrrolo[3;2,4-Dichl;5H-Pyrrolo[2,3-d]pyriMidine, 2,4-dichloro-;5H-Pyrrolo[3,2-d]pyriMidine,2,4-dichloro- | | CAS: | 63200-54-4 | | MF: | C6H3Cl2N3 | | MW: | 188.01 | | EINECS: | 810-549-5 | | Product Categories: | Heterocycles;Heterocycle-Pyrimidine series;CHIRAL CHEMICALS | | Mol File: | 63200-54-4.mol | ![2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE Structure](CAS/GIF/63200-54-4.gif) |
| | 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE Chemical Properties |
| Melting point | 226-228 °C(Solv: water (7732-18-5); methanol (67-56-1)) | | Boiling point | 306.2±24.0 °C(Predicted) | | density | 1.675±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 10.67±0.40(Predicted) | | Appearance | White to yellow Solid | | InChI | InChI=1S/C6H3Cl2N3/c7-5-4-3(1-2-9-4)10-6(8)11-5/h1-2,9H | | InChIKey | MVTLFDKTYGKJEX-UHFFFAOYSA-N | | SMILES | C1(Cl)=NC(Cl)=C2NC=CC2=N1 |
| HazardClass | IRRITANT | | HS Code | 2933599590 |
| | 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE Usage And Synthesis |
| Uses | 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine is an organic intermediate. It can be used to prepare a pyrrolo[3,2-d]pyrimidinone analogue, which is a potent DPP-IV inhibitor that is able to effectively lower blood glucose without causing risks such as weight gain and hypoglycaemia, and achieve prolonged therapeutic control of blood glucose. | | Synthesis | 1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (0.38 g, 2.52 mmol) was used as starting material and suspended in phosphorus trichloride (30 mL). The suspension was heated to 120°C and the reaction was carried out for 6 h, during which the mixture gradually changed to a clarified homogeneous solution. Upon completion of the reaction, the mixture was cooled to room temperature and the excess phosphorus trichloride was subsequently removed under vacuum. The residue was cooled in an ice bath and cold ammonium hydroxide solution (30 mL, pH = 8) was slowly added and stirred under this condition for 30 minutes. At the end of the reaction, the precipitate was collected by filtration and washed with cold water. Finally, the resulting solid was dried under vacuum to afford the target product 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (0.33 g, 70% yield). | | References | [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 821 - 827
[2] Patent: WO2009/62258, 2009, A1. Location in patent: Page/Page column 98
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2113 - 2122
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4354 - 4363
[5] Patent: US2016/257696, 2016, A1. Location in patent: Paragraph 0069-0070 |
| | 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE Preparation Products And Raw materials |
| Raw materials | 5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyriMidine-->1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion-->Ammonia | | Preparation Products | 2-CHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE-->5H-Pyrrolo[3,2-d]pyrimidine, 2-chloro-5-[[2-(trimethylsilyl)ethoxy]methyl]--->4-(2-Chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)morpholine-->2-chloro-5-ethyl-3H-pyrrolo[3,2-
d]pyrimidin-4(5H)-one-->5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyriMidine |
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