| Identification | More | [Name]
2, 4-DICHLORO-5-IODOPYRIMIDINE | [CAS]
13544-44-0 | [Synonyms]
5-Iodo-2,4-dichloropyrimidine | [EINECS(EC#)]
621-974-9 | [Molecular Formula]
C4HCl2IN2 | [MDL Number]
MFCD01898087 | [Molecular Weight]
274.87 | [MOL File]
13544-44-0.mol |
| Chemical Properties | Back Directory | [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) |
| Safety Data | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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