| Identification | More | [Name]
4-Chloropyrrolo[2,3-d]pyrimidine | [CAS]
3680-69-1 | [Synonyms]
4-CHLORO-1H-PYRROLO(2,3-D)PYRIMIDINE
4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE
4-CHLOROPYRROLO[2,3-D]PYRIMIDINE
6-CHLORO-7-DEAZAPURINE
3-d)pyrimidine,4-chloro-7h-pyrrolo(
6-CHLORO-7-DEAZAPURINE 4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE 4-CHLORO-1H-PYRROLO[2,3-D]PYRIMIDINE 4-CHLOROPYRROLO[2,3-D]PYRIMIDINE 6-CHLORO-7-DEAZAPURIN
4-Chloro-1H-pyrrolo[2,3-d]pyrimidine4-Chloropyrrolo[2,3-d]pyrimidine
6-Chloro-7-deazapurin
4-CHLORO-4H-PYRROLO[2,3-D]PYRIMIDINE
6-CHLORO-7-DEAZAPURINE 98.5%
6-Chloro-7-deazapurine, 4-Chloro-1H-pyrrolo[2,3-d]pyrimidine
4-METHYL-2,5-DIAMINETHIAZOLE
7H-pyrrolo[2,3-d]pyrimidine, 4-chloro-
4-chloro-7H-pyrrolo[2,3-d]pyrimidine/6-Chloro-7-deazapurine | [EINECS(EC#)]
628-079-2 | [Molecular Formula]
C6H4ClN3 | [MDL Number]
MFCD01686865 | [Molecular Weight]
153.57 | [MOL File]
3680-69-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Lightbrown to brown crystalline powder | [Melting point ]
188-194 °C | [Boiling point ]
289.2±50.0 °C(Predicted) | [density ]
1.61±0.1 g/cm3(Predicted) | [vapor pressure ]
0Pa at 25℃ | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Soluble in DMSO, ethyl acetate and methanol. | [form ]
Crystalline Powder | [pka]
11.42±0.20(Predicted) | [color ]
White to tan | [InChI]
InChI=1S/C6H4ClN3/c7-5-4-1-2-8-6(4)10-3-9-5/h1-3H,(H,8,9,10) | [InChIKey]
BPTCCCTWWAUJRK-UHFFFAOYSA-N | [SMILES]
C1=NC(Cl)=C2C=CNC2=N1 | [LogP]
0.858 at 30℃ | [CAS DataBase Reference]
3680-69-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H301 | [Precautionary statements ]
P301+P310 | [Hazard Codes ]
Xi,T,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R25:Toxic if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37:Wear suitable gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 2811 6.1/PG 3 | [WGK Germany ]
3 | [RTECS ]
UY9360000 | [TSCA ]
No | [REACH Registrations]
Active | [HazardClass ]
IRRITANT | [PackingGroup ]
Ⅲ | [HS Code ]
29335900 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
Lightbrown to brown crystalline powder | [Application]
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine is an important heterocyclic compound and can be used for preparing JAK inhibitors Tofacitinib, Ruxolitinib, SHR0302 and other medicaments.
| [Chemical Reactivity]
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine undergos nucleophilic substitution reactions.
| [Synthesis]
The preparation process of pyrimidine includes the first α -alkylation reaction between diethyl malonate and allyl bromide, and the subsequent cyclization reaction with amidine to obtain a six-membered ring of bislactam. The chlorination of carbonyl with phosphorus oxychloride to obtain dichloro pyrimidine ring, followed by the oxidation of the terminal double bond with potassium osmate hydrate and sodium periodate to obtain the aldehyde group. The final reaction with ammonia water to produce SNAr/cyclization reaction, a five-step reaction, total yield of 45.8% to obtain 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.
![4-Chloro-7H-pyrrolo[2,3-d]pyrimidine](/NewsImg/2023-10-18/6383323147119370063141800.jpg "4-Chloro-7H-pyrrolo[2,3-d]pyrimidine")
|
| Questions And Answer | Back Directory | [Uses]
4-Chloro-7H-pyrrolo[2,3-d] pyrimidine is an important pharmaceutical intermediate, which is widely used in the synthesis of many pharmaceutical intermediates at home and abroad. Including CP690550, CGP76030 and so on, 4-Chloro-7H-pyrrolo[2,3-d] pyrimidine was the scaffold for many commercially available drugs. Also, 4-Chloro-7H-pyrrolo[2,3-d] pyrimidine was the intermediate of the bulk drug, Tofatinib, which was widely used in treatment of adult patients with moderate to severe rheumatoid arthritis with inadequate or intolerant methotrexate response.
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JINANHAIHAO Gold
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Alfa Aesar
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