16372-08-0

Basic information

• Product Name: 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine
• Synonyms: 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine;4-chloro-5H,6H,7H-pyrrolo[2,3-d]pyriMidine;5H-Pyrrolo[2,3-d]pyriMidine,4-chloro-6,7-dihydro-
• CAS NO: 16372-08-0
• Molecular Formula: C6H6ClN3
• Molecular Weight: 155.58
• Product Categories: CHIRAL CHEMICALS;Heterocycle-Pyrimidine series
• Mol File: 16372-08-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 158.5-160 °C
• Boiling Point: 311.9 °C at 760 mmHg
• Flash Point: 142.5 °C
• Appearance: /
• Density: 1.377 g/cm³
• Refractive Index: 1.592
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.69±0.20(Predicted)
• CAS DataBase Reference: 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine(16372-08-0)
• EPA Substance Registry System: 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine(16372-08-0)

Safety Data

• Hazardous Substances Data: 16372-08-0(Hazardous Substances Data)

Usage

Description

4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine is a pyrolopyrimidine derivative, a type of heterocyclic compound with a unique chemical structure that features a pyrrolo fused with a pyrimidine ring. 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine is characterized by the presence of a chlorine atom at the 4-position and a partially saturated 6,7-dihydro ring system. Its distinctive molecular structure endows it with specific chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine is used as an intermediate in the synthesis of the antibiotic tubercidin (7-deazadenosine) for its role in the development of this important antimicrobial agent. Tubercidin is a potent antibiotic effective against a range of bacterial infections, including tuberculosis. The pyrolopyrimidine derivative contributes to the structural framework of tubercidin, which is essential for its biological activity and therapeutic efficacy.

InChI:InChI=1/C6H6ClN3/c7-5-4-1-2-8-6(4)10-3-9-5/h3H,1-2H2,(H,8,9,10)

Upstream product

• 910399-87-0 C₆H₇Cl₂N₃ 
• 1578264-09-1 C₁₄H₁₅Cl₂N₃O 
• 853680-75-8 methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl ester 
• 853680-74-7 2-(4,6-dichloropyrimidin-5-yl)ethanol 
• 171096-33-6 methyl 2-(4,6-dichloropyrimidin-5-yl)acetate 

Downstream Products

• 1578265-15-2 C₁₇H₁₅FN₄O₃ 
• 1578265-14-1 C₁₇H₁₅FN₄O₃ 
• 1610452-24-8 [2-[4-(6,7-dihydro-5H-pyrrolo[2.3-d]pyrimidin-4-yl)-piperazin-1-yl]-2-(4-trifluoromethylphenyl)-ethyl]-dimethylamine 

Relevant articles and documents

1-(2-hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile derivatives as potent and tissue selective androgen receptor modulators

We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.