| Identification | More | [Name]
5-Amino-4,6-dichloropyrimidine | [CAS]
5413-85-4 | [Synonyms]
4,6-DICHLORO-5-PYRIMIDINAMINE
4,6-DICHLOROPYRIMIDIN-5-AMINE
4,6-DICHLOROPYRIMIDIN-5-YLAMINE
5-AMINO-4,6-DICHLOROPYFIMIDINE
5-AMINO-4,6-DICHLOROPYRIMIDINE
5-PYRIMIDINAMINE, 4,6-DICHLORO-
AKOS 91433
TIMTEC-BB SBB003920
4,6-Dichloro-5-aminopyrimidine
4,6-dichloro-5-pyrimidinamin
Pyrimidine, 5-amino-4,6-dichloro-
5-AMINO-4,6-DICHLORPYRIMIDIN 97%
5-Amino-4,6-dichloro
5-amine-4,6-dichloropyrimidine
5-Amino-4,6-dichloropyrimidine, 98+% | [EINECS(EC#)]
226-503-7 | [Molecular Formula]
C4H3Cl2N3 | [MDL Number]
MFCD00006108 | [Molecular Weight]
163.99 | [MOL File]
5413-85-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellowish-brown crystals or powder | [Melting point ]
145-148 °C (lit.) | [Boiling point ]
270.44°C (rough estimate) | [density ]
1.6662 (rough estimate) | [refractive index ]
1.6300 (estimate) | [storage temp. ]
2-8°C | [solubility ]
slightly soluble | [form ]
Crystals or Powder | [pka]
-3.01±0.26(Predicted) | [color ]
Yellow-brown | [Water Solubility ]
slightly soluble | [Sensitive ]
Moisture Sensitive | [BRN ]
126885 | [InChI]
1S/C4H3Cl2N3/c5-3-2(7)4(6)9-1-8-3/h1H,7H2 | [InChIKey]
NIGDWBHWHVHOAD-UHFFFAOYSA-N | [SMILES]
Nc1c(Cl)ncnc1Cl | [CAS DataBase Reference]
5413-85-4(CAS DataBase Reference) | [NIST Chemistry Reference]
5-Amino-4,6-dichloropyrimidine(5413-85-4) | [EPA Substance Registry System]
5413-85-4(EPA Substance) |
| 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:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
10-21 | [TSCA ]
Yes | [HS Code ]
29335900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Ethyl acetate-->Nitric acid-->Phosphorus oxitrichloride-->Hexane-->Trifluoroacetic acid-->Stannous chloride dihydrate-->N,N-Diisopropylethylamine-->4,6-Dihydroxypyrimidine-->5-AMINO-4,6-DIHYDROXYPYRIMIDINE-->4,6-Dichloro-5-nitropyrimidine | [Preparation Products]
4,5-Diaminopyrimidine-->5-Pyrimidinamine, 1,4,5,6-tetrahydro--->2-(5-AMINO-6-CHLORO-PYRIMIDIN-4-YLAMINO)-ETHANOL-->6-CHLORO-N4-(4-CHLOROPHENYL)-4,5-PYRIMIDINEDIAMINE-->4-(5-AMINO-6-CHLORO-4-PYRIMIDINYL)-1-PIPERAZINECARBOXYLIC ACID 1,1-DIMETHYLETHYL ESTER-->6-chloro-N4-ethylpyrimidine-4,5-diamine-->(R)-1-((5-aMino-6-chloropyriMidin-4-yl)aMino)propan-2-ol-->4-CHLORO-6-HYDRAZINO-PYRIMIDIN-5-YLAMINE |
| Hazard Information | Back Directory | [Chemical Properties]
Yellowish-brown crystals or powder | [Uses]
5-Amino-4,6-dichloropyrimidine was used in the synthesis of:
- oxepane ring containing monocyclic, conformationally restricted bicyclic and spirocyclic nucleosides
- conformationally locked bicyclo[2.2.1]heptane/oxa-bicyclo[3.2.1]octane nucleosides
- N(7)-substituted purines
- chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine
- 9-alkyl-6-substituted-purine analogs, potent anticonvulsant agents
- pyrimido-oxazepines in a three-step process with microwave heating at 150°C
| [Uses]
An intermediate in the production of many biological inhibitors. | [Synthesis]
GENERAL METHODS: 10% Pd/C catalyst (0.05 g) was added to a solution of 4,6-dichloro-5-nitropyrimidine (4.48 mmol) in ethyl acetate (EA, 20 mL) in a Parr hydrogenation reactor. Subsequently, the air in the reactor was replaced with nitrogen three times and the hydrogenation reaction was carried out at room temperature and at atmospheric pressure. Upon completion of the reaction, the reaction solution was filtered through a diatomaceous earth filter to remove the Pd/C catalyst, and the filtrate was concentrated to give the target product 4,6-dichloro-5-aminopyrimidine [46]. | [References]
[1] Journal of Labelled Compounds and Radiopharmaceuticals, 2008, vol. 51, # 1, p. 54 - 58
[2] Tetrahedron, 1988, vol. 44, # 19, p. 6207 - 6216
[3] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 212 - 228
[4] Synlett, 2010, # 20, p. 3019 - 3022
[5] Synthetic Communications, 2007, vol. 37, # 16, p. 2777 - 2786 |
|
|