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| | 2-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE Basic information |
| | 2-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE Chemical Properties |
| density | 1.531±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 11.18±0.50(Predicted) | | form | solid | | Appearance | Off-white to light brown Solid | | InChI | InChI=1S/C6H4ClN3/c7-6-9-3-4-1-2-8-5(4)10-6/h1-3H,(H,8,9,10) | | InChIKey | HJOQGBBHVRYTDX-UHFFFAOYSA-N | | SMILES | C1(Cl)=NC=C2C=CNC2=N1 |
| Hazard Codes | Xi,T | | Risk Statements | 25 | | Safety Statements | 45-24/25 | | RIDADR | UN2811 | | WGK Germany | WGK 3 | | Hazard Note | Irritant | | HS Code | 29339900 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral |
| | 2-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE Usage And Synthesis |
| Uses | An intermediate pyrrolo-pyrimidine compound, 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine can be used in the preparation of tyrosine kinase inhibitors, particularly oral signal transducers and activators of transcription 6 (STAT6) inhibitors. | | Uses | An intermediate pyrrolo-pyrimidine compound used in the preparation of tyrosine kinase inhibitors, particularly oral signal transducers and activators of transcription 6 (STAT6) inhibitors. | | Synthesis | The general procedure for the synthesis of 2-chloro-7H-pyrrolo[2,3-d]pyrimidines from 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidines is as follows: zinc powder (8700.0 g, 133 mol, 10.0 eq.) was added in batches to glacial acetic acid (3.3 L, 53.2 mol, 4.0 eq.), followed by addition of acetonitrile (30.0 L) to form a reaction mixture. The reaction mixture was cooled to 25 °C and then filtered. The filtrate was concentrated under reduced pressure and then added to 30 L of ice water to precipitate the product. The mixture was warmed to 80 °C and kept at this temperature for 14 hours. Upon completion of the reaction, a pink solid was obtained. The solid was collected by filtration and the cake was washed with water (5 L x 3 times) and dried to give 1501.7 g of white solid in 73.54% yield. | | References | [1] Patent: CN105949196, 2016, A. Location in patent: Paragraph 0044; 0065; 0083-0087
[2] Patent: CN105859726, 2016, A. Location in patent: Paragraph 0030; 0031; 0032
[3] Patent: WO2010/7116, 2010, A2. Location in patent: Page/Page column 91-92
[4] Patent: WO2010/7114, 2010, A2. Location in patent: Page/Page column 125-126
[5] Patent: JP2016/124825, 2016, A |
| | 2-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE Preparation Products And Raw materials |
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