|
|
| | 2, 4-DICHLORO-5-IODOPYRIMIDINE Basic information |
| Product Name: | 2, 4-DICHLORO-5-IODOPYRIMIDINE | | Synonyms: | 5-Iodo-2,4-dichloropyrimidine;2,4-Dichloro-5-iodopyrimidine;2,4-Dichloro-5-iodo-1,3-diazine;2,4-Dichloro-5-iodopyriMidine, 95+%;Pyrimidine, 2,4-dichloro-5-iodo-;2,4-Dichloro-5-iodopyrimidine 95%;2,4-Dichloro-5-iodopyrimidine>;oro-5-iodopyrimidine | | CAS: | 13544-44-0 | | MF: | C4HCl2IN2 | | MW: | 274.87 | | EINECS: | 621-974-9 | | Product Categories: | Halides;Pyrazines, Pyrimidines & Pyridazines;pharmacetical;Organohalides;Pyrimidine;Pyrimidines;Pyrimidine series;Heterocycle-Pyrimidine series | | Mol File: | 13544-44-0.mol |  |
| | 2, 4-DICHLORO-5-IODOPYRIMIDINE Chemical Properties |
| Melting point | 68.0 to 72.0 °C | | Boiling point | 310.2±22.0 °C(Predicted) | | density | 2?+-.0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | solubility | soluble in Methanol | | form | powder to crystal | | pka | -4.19±0.29(Predicted) | | color | White to Gray to Brown | | InChI | 1S/C4HCl2IN2/c5-3-2(7)1-8-4(6)9-3/h1H | | InChIKey | RGJNPJRAXMSHKN-UHFFFAOYSA-N | | SMILES | Clc1ncc(I)c(Cl)n1 | | CAS DataBase Reference | 13544-44-0(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22-37/38-41 | | Safety Statements | 26-39 | | RIDADR | 2811 | | WGK Germany | 3 | | HazardClass | 6.1 | | 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
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| | 2, 4-DICHLORO-5-IODOPYRIMIDINE Usage And Synthesis |
| Chemical Properties | Off-white powder | | Uses | 2,4-Dichloro-5-iodopyrimidine can be used as a reagent to synthesize dipeptidyl peptidase IV inhibitors. It is also used to synthesize pyrimidine VLA-4 antagonists. | | Synthesis | The general procedure for the synthesis of 2,4-dichloro-5-iodopyrimidine from 5-iodouracil is as follows:
1. Preparation of intermediate 1: 2,4-dichloro-5-iodopyrimidine
- To a suspension of N,N-dimethylaniline (11.0 mL) in 5-iodouracil (10.0 g, 42 mmol), phosphorus oxychloride (POCl3, 64.4 g, 39.2 mL, 420 mmol) was added.
- The reaction mixture was heated to 90 °C and stirred at this temperature for 90 min.
- After the reaction was completed, it was cooled to room temperature and the excess POCl3 was removed by evaporation.
- The residue was slowly poured into an ice-water mixture and stirred for 2 h. The crystalline precipitate was collected by filtration and washed with cold water.
- The crude product was dissolved in ethyl acetate and extracted sequentially with aqueous sodium bicarbonate and aqueous sodium sulfite.
- The organic phase was dried with anhydrous sodium sulfate, filtered and the solvent was evaporated.
- The residue was purified by column chromatography to afford 2,4-dichloro-5-iodopyrimidine (10.6 g, 92% yield). The structure of the product was determined by 1H-NMR.
- The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3): δ 8.90 (s, 1H). | | References | [1] Patent: EP1878726, 2008, A1. Location in patent: Page/Page column 32
[2] Patent: WO2007/71455, 2007, A1. Location in patent: Page/Page column 146
[3] Patent: US2007/232632, 2007, A1. Location in patent: Page/Page column 55; 56
[4] Patent: WO2008/155140, 2008, A1. Location in patent: Page/Page column 108
[5] Tetrahedron, 2000, vol. 56, # 27, p. 4777 - 4792 |
| | 2, 4-DICHLORO-5-IODOPYRIMIDINE Preparation Products And Raw materials |
|