Introduction：Basic information about 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine CAS 3680-69-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine Basic information
| Product Name: | 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine |
| Synonyms: | 4-CHLORO-1H-PYRROLO(2,3-D)PYRIMIDINE;4-CHLOROPYRROLO[2,3-D]PYRIMIDINE;4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE;6-CHLORO-7-DEAZAPURINE;6-CHLORO-7-DEAZAPURINE 4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE 4-CHLORO-1H-PYRROLO[2,3-D]PYRIMIDINE 4-CHLOROPYRROLO[2,3-D]PYRIMIDINE 6-CHLORO-7-DEAZAPURIN;4-Chloro-1H-pyrrolo[2,3-d]pyrimidine4-Chloropyrrolo[2,3-d]pyrimidine;6-Chloro-7-deazapurin;4-CHLORO-4H-PYRROLO[2,3-D]PYRIMIDINE |
| CAS: | 3680-69-1 |
| MF: | C6H4ClN3 |
| MW: | 153.57 |
| EINECS: | 628-079-2 |
| Product Categories: | Fused Ring Systems;Heterocyclic Building Blocks;Heterocycle-Pyrimidine series;Baricitinib;Ruxolitinib;Tofacitinib;Heterocycles series;Halides;Pyrimidine;Heterocycles;Bases & Related Reagents;Intermediates;Nucleotides;Heterocyclic Compounds;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;CHIRAL CHEMICALS;Naphthyridine,Quinoline;3680-69-1 |
| Mol File: | 3680-69-1.mol |
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4-Chloro-7H-pyrrolo[2,3-d]pyrimidine Chemical Properties
| Melting point | 188-194 °C |
| Boiling point | 289.2±50.0 °C(Predicted) |
| density | 1.61±0.1 g/cm3(Predicted) |
| vapor pressure | 0Pa at 25℃ |
| storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
| solubility | Soluble in DMSO, ethyl acetate and methanol. |
| form | Crystalline Powder |
| pka | 11.42±0.20(Predicted) |
| color | White to tan |
| InChI | InChI=1S/C6H4ClN3/c7-5-4-1-2-8-6(4)10-3-9-5/h1-3H,(H,8,9,10) |
| InChIKey | BPTCCCTWWAUJRK-UHFFFAOYSA-N |
| SMILES | C1=NC(Cl)=C2C=CNC2=N1 |
| LogP | 0.858 at 30℃ |
| CAS DataBase Reference | 3680-69-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi,T,Xn |
| Risk Statements | 36/37/38-25-20/21/22 |
| Safety Statements | 26-37-45-36 |
| RIDADR | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | UY9360000 |
| TSCA | No |
| HazardClass | IRRITANT |
| PackingGroup | Ⅲ |
| HS Code | 29335990 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral |
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine Usage And Synthesis
| Uses | 4-Chloro-7H-pyrrolo[2,3-d] pyrimidine is an important pharmaceutical intermediate, which is widely used in the synthesis of many pharmaceutical intermediates at home and abroad. Including CP690550, CGP76030 and so on, 4-Chloro-7H-pyrrolo[2,3-d] pyrimidine was the scaffold for many commercially available drugs. Also, 4-Chloro-7H-pyrrolo[2,3-d] pyrimidine was the intermediate of the bulk drug, Tofatinib, which was widely used in treatment of adult patients with moderate to severe rheumatoid arthritis with inadequate or intolerant methotrexate response. |
| Chemical Properties | Lightbrown to brown crystalline powder |
| Uses | 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine is used in the manufacture of Tofacitinib citrate. |
| Application | 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine is an important heterocyclic compound and can be used for preparing JAK inhibitors Tofacitinib, Ruxolitinib, SHR0302 and other medicaments. |
| Chemical Reactivity | 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine undergos nucleophilic substitution reactions. |
| Synthesis | The preparation process of pyrimidine includes the first α -alkylation reaction between diethyl malonate and allyl bromide, and the subsequent cyclization reaction with amidine to obtain a six-membered ring of bislactam. The chlorination of carbonyl with phosphorus oxychloride to obtain dichloro pyrimidine ring, followed by the oxidation of the terminal double bond with potassium osmate hydrate and sodium periodate to obtain the aldehyde group. The final reaction with ammonia water to produce SNAr/cyclization reaction, a five-step reaction, total yield of 45.8% to obtain 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. |
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine Preparation Products And Raw materials
| Raw materials | Sodium-->Phosphorus oxitrichloride-->Potassium carbonate-->Ammonium chloride-->Ethyl cyanoacetate-->Thiourea-->Sodium iodide-->Bromoacetaldehyde diethyl acetal-->RANEY NICKEL-->Pyrrolo[2,3-d]pyrimidin-4-ol |
| Preparation Products | 7H-Pyrrolo[2,3-d]pyrimidine-->5-iodo-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine-->4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile-->(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate-->4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine-->5-IODOTUBERCIDIN |
