ChemicalBook > CAS DataBase List > 4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINE

4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINE

Product Name: 4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINE
CAS No.: 84905-80-6
Chemical Name: 4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINE
Synonyms: SW-58;SWF-58;4-CHLORO-5H-PYRROLO[3;6-chloro-9-deaza-7H-puri;4-Chloro-5H-pyrrolo[3,2-d...;4-chloro-5H-pyrrolo[2,3-c]pyridine;4-chloro-1H-pyrrolo[3,2-d]pyriMidine;5H-Pyrrolo3,2-dpyrimidine, 4-chloro-;4-Chloro-5H-pyrrol[3,2-d] pyrimidine;4-CHLORO-5H-PYROLO-[3,2-d]PYRIMIDINE
CBNumber: CB6771371
Molecular Formula: C6H4ClN3
Formula Weight: 153.57
MOL File: 84905-80-6.mol

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4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINE Property

Melting point:: 186-188 °C (decomp)(Solv: water (7732-18-5); ethanol (64-17-5))
Boiling point:: 325.9±22.0 °C(Predicted)
Density: 1.531±0.06 g/cm3(Predicted)
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
form: solid
pka: 11.58±0.40(Predicted)
color: Off-white
InChI: InChI=1S/C6H4ClN3/c7-6-5-4(1-2-8-5)9-3-10-6/h1-3,8H
InChIKey: ZGJDDWOXVGDTSP-UHFFFAOYSA-N
SMILES: C1=NC(Cl)=C2NC=CC2=N1

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Safety

HazardClass: IRRITANT
HS Code: 2933599590

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

TRC

Product number: C380040
Product name: 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine
Packaging: 500mg
Price: $195
Updated: 2021/12/16

SynQuest Laboratories

Product number: 3H32-5-V4
Product name: 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine
Purity: 97%
Packaging: 10g
Price: $155
Updated: 2021/12/16

Apolloscientific

Product number: OR46059
Product name: 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine
Packaging: 1g
Price: $21
Updated: 2021/12/16

Matrix Scientific

Product number: 054205
Product name: 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine
Purity: >95%
Packaging: 1g
Price: $34
Updated: 2021/12/16

SynQuest Laboratories

Product number: 3H32-5-V4
Product name: 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine
Purity: 97%
Packaging: 5G
Price: $95
Updated: 2021/12/16

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4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINE Chemical Properties,Usage,Production

Description

4-Chloro-5H-pyrrolo[3,2-d]pyrimidine is a purine analog that inhibits the growth of bacteria by binding to the enzyme DNA gyrase. It has been shown to be effective against staphylococcus and Mycobacterium tuberculosis.

Uses

4-Chloro-5H-pyrrolo[3,2-d]pyrimidine is a chlorinated pyrrolopyrimidine used in the preparation of compounds with antibacterial and antitumor activities.

Application

4-Chloro-5H-pyrrolo[3,2-d]pyrimidine binds to the enzyme DNA gyrase and prevents it from breaking down the bacterial DNA. This drug also has antimycobacterial activity due to its ability to bind to the enzyme RNA polymerase.

Synthesis

5655-01-6

84905-80-6

Step 4: Preparation of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (32e). 3H,5H-pyrrolo[3,2-d]pyrimidin-4-one (32d) (31.08 g, 230 mmol) was placed under a nitrogen atmosphere and phosphoryl chloride (60 mL, 644 mmol) was added. The reaction mixture was heated to reflux for 1 h, during which the mixture was observed to transform into a black homogeneous solution. Upon completion of the reaction, the mixture was cooled in an ice-water bath and subsequently slowly poured into crushed ice (775 mL) under stirring. The pH of the aqueous solution was slowly adjusted to about 8 with concentrated ammonia (225 mL) while keeping the mixture cool. The resulting precipitate was collected by vacuum filtration and washed with cold water. The solid was transferred to a drying tray and dried under vacuum at 110 °C to afford 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (32e) (31.48 g, 89% yield) as a dark gray solid. To obtain an analytically pure sample, it was purified by silica gel column chromatography (eluent: EtOAc-hexane, 35:65) and the relevant fractions were collected and concentrated. Grinding of the solid with EtOAc-MeOH mixed solvent afforded an off-white solid 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (32e) with a melting point >150 °C (decomposition).1H NMR (DMSO-d6) δ 12.43 (s, D2O exchangeable, 1H), 8.61 (s, 1H), 7.97 (dd, J = 2.8, 2.8 Hz; D2O-exchangeable to d, 1H), 6.72 (dd, J = 1.7, 3.5 Hz; D2O-exchangeable to d, 1H).13C NMR (DMSO-d6) δ 151.30, 149.58, 142.12, 134.83, 124.32, 102.70.IR (pure sample) 3128, 3078, 2979, 1621 cm-1. MS (ES+) m/z 154.01 (100%, [M+H]+), 156.01 (33%). Elemental analysis (C6H4N3Cl) Calculated values: C, 46.93; H, 2.63; N, 27.36; Cl, 23.09. Measured values: C, 47.10; H, 2.79; N, 27.15; Cl, 22.93.

References

[1] Organic Process Research and Development, 2009, vol. 13, # 5, p. 928 - 932
[2] Patent: WO2014/78778, 2014, A2. Location in patent: Page/Page column 105
[3] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 8658 - 8669
[4] Patent: WO2008/70507, 2008, A2. Location in patent: Page/Page column 150-151
[5] Patent: US2012/202785, 2012, A1. Location in patent: Page/Page column 129

4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINE manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: 4-Chloro-5H-pyrrolo[3,2-d]pyriMidine 84905-80-6
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 20T
Release date: 2020-05-14

Career Henan Chemical Co

Product: 4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINE 84905-80-6
Price: US $500.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1ton
Release date: 2018-08-04

84905-80-6, 4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINERelated Search:

tert-butyl 7-oxo-2,6-diazaspiro[3.4]octane-2-carboxylate 1-Benzylazetidin-3-ol 4-Chloro-5-fluoro-2-(Meth... Acetic acid, [(5-chloro-2-pyridinyl)aMino]oxo- Methyl (R)-1-Boc-4,4-difluoropyrrolidine-2-carboxylate 6-BROMO-4-INDOLECARBOXYLIC ACID METHYL ESTER 6-Methoxyindole 7-Azabicyclo[2,2,1]heptane hydrochloride Diethyl 1H-pyrrole-2,4-dicarboxylate 1H-PYRROLO[2,3-B]PYRIDIN-5-OL 1-Hydroxy-1-cyclopropanecarboxylic acid 3-BroMo-5-nitro-1H-pyrazo... 4-Bromo-7-azaindole 4-Chloro-7-azaindole 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester tert-butyl (1R,2S,5S)-2-aMino-5-(diMethylcarbaMoyl)cyclohexylcarbaMate DL-7-Azatryptophan Monohydrate 1H-PYRROLO[2,3-B]PYRIDINE-4-CARBOXYLIC ACID

4-CHLORO-5H-PYRROLO[3,2-D] PYRIMIDINE

4-Chloro-5H-pyrrol[3,2-d] pyrimidine

5H-Pyrrolo3,2-dpyrimidine, 4-chloro-

4-chloro-5H-pyrrolo[2,3-c]pyridine

4-Chloro-5H-pyrrolo[3,2-d...

6-chloro-9-deaza-7H-purine, 4-chloro-3H,5H-pyrrolo[3,2-d]pyriMidine, 4-Chloropyrrolo<3,2-d>pyriMidine

4-chloro-1H-pyrrolo[3,2-d]pyriMidine

6-chloro-9-deaza-7H-puri

4-CHLORO-5H-PYRROLO[3

SWF-58

SW-58

4-CHLORO-5H-PYROLO-[3,2-d]PYRIMIDINE

84905-80-6

4905-80-6

Heterocycle-Pyrimidine series

CHIRAL CHEMICALS

Heterocycles series