| Identification | More | [Name]
4-Amino-6-chloropyrimidine | [CAS]
5305-59-9 | [Synonyms]
4-AMINO-6-CHLOROPYRIMIDINE
6-CHLORO-PYRIMIDIN-4-YLAMINE
4-Pyrimidinamine, 6-chloro-(9CI)
2-CHLORO-6-AMINOPYRIMIDINE
6-Chloro-4-pyrimidinamine
6-CHLORO-PYRIMIDIN-4-YLAMINE 98%
6-Chloropyrimidin-4-amine
6-Chloropyrimidine-4-amine | [EINECS(EC#)]
664-284-3 | [Molecular Formula]
C4H4ClN3 | [MDL Number]
MFCD00053576 | [Molecular Weight]
129.55 | [MOL File]
5305-59-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale Yellow Solid | [Melting point ]
215-216°C | [Boiling point ]
289.0±20.0 °C(Predicted) | [density ]
1.437±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO | [form ]
Solid | [pka]
2.16±0.10(Predicted) | [color ]
Pale Yellow | [InChI]
InChI=1S/C4H4ClN3/c5-3-1-4(6)8-2-7-3/h1-2H,(H2,6,7,8) | [InChIKey]
DUKKRSPKJMHASP-UHFFFAOYSA-N | [SMILES]
C1=NC(Cl)=CC(N)=N1 | [CAS DataBase Reference]
5305-59-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3 | [Hazard Note ]
Harmful | [HazardClass ]
IRRITANT | [HS Code ]
29335900 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale Yellow Solid | [Anticancer Research]
4-Amino-6-chloropyrimidine has been shown to inhibit the proliferation of cancer cells in vitro and in vivo, without affecting normal cells. 4-Amino-6-chloropyrimidine also inhibits kinase activity and protein synthesis in cancer cells. This drug has a potent inhibitory effect on cell proliferation. | [Synthesis]
The general procedure for the synthesis of 4-amino-6-chloropyrimidine from 4,6-dichloropyrimidine was as follows: to a suspension of 4,6-dichloropyrimidine (3.0 g, 20 mmol) in isopropanol (40 mL) was slowly added the appropriate amine, with the rate of addition being controlled so as to maintain the internal temperature of the reaction system at no more than 40°C. The reaction mixture was stirred continuously for 1 hour at 25°C. After addition, the reaction mixture was stirred continuously at 25 °C for 1 hour. Upon completion of the reaction, water (30 mL) was added and the resulting suspension was cooled to 0 °C in an ice bath. The precipitated product was collected by filtration and washed sequentially with pre-cooled isopropanol/water solvent mixture (V/V=2:1, 50 mL) and pure water. Finally, the resulting solid product was dried under vacuum to obtain the target compound 4-amino-6-chloropyrimidine. | [References]
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7066 - 7083
[2] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 11 - 20
[3] Patent: WO2012/35039, 2012, A1. Location in patent: Page/Page column 84
[4] Patent: US2012/15943, 2012, A1. Location in patent: Page/Page column 54
[5] ChemMedChem, 2017, vol. 12, # 16, p. 1390 - 1398 |
|
|