1245811-22-6

Basic information

• Product Name: 2-Chloro-3,7-dihydro-4H-pyrrolo[2,3-d]pyriMidin-4-one
• Synonyms: 2-Chloro-3,7-dihydro-4H-pyrrolo[2,3-d]pyriMidin-4-one;2-Chloro-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one;2-chloro-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS NO: 1245811-22-6
• Molecular Formula: C₆H₄ClN₃O
• Molecular Weight: 169.56846
• Mol File: 1245811-22-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 404.6±37.0 °C(Predicted)
• Appearance: /
• Density: 1.82±0.1 g/cm3(Predicted)
• PKA: 15.39±0.20(Predicted)
• CAS DataBase Reference: 2-Chloro-3,7-dihydro-4H-pyrrolo[2,3-d]pyriMidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-3,7-dihydro-4H-pyrrolo[2,3-d]pyriMidin-4-one(1245811-22-6)
• EPA Substance Registry System: 2-Chloro-3,7-dihydro-4H-pyrrolo[2,3-d]pyriMidin-4-one(1245811-22-6)

Safety Data

• Hazardous Substances Data: 1245811-22-6(Hazardous Substances Data)

Usage

Uses

2-Chloro-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one can be used to prepare antitumor agents.

Upstream product

• 52133-67-2 ethyl 2-cyano-4,4-diethoxybutyrate 
• 90213-66-4 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine 
• 39929-79-8 pyrrolo<2,3-d>pyrimidin-2,4-dione 

Downstream Products

• 1245811-23-7 tert-butyl 2-chloro-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine-7-carboxylate 
• 1377432-73-9 2-((2-((R)-3-aminopiperidin-1-yl)-4-oxo-6-(pyridin-3-yl)-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile 
• 1377432-72-8 2-((2-((R)-3-aminopiperidin-1-yl)-6-(4-fluorophenyl)-4-oxo-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile 
• 1377432-71-7 2-((2-((R)-3-aminopiperidin-1-yl)-4-oxo-6-(4-(trifluoromethyl)phenyl)-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile 
• 1377432-70-6 2-((2-((R)-3-aminopiperidin-1-yl)-6-bromo-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile 
• 1377432-89-7 tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-4-oxo-6-(pyridin-3-yl)-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)piperidin-3-yl)carbamate 
• 1377432-88-6 tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-6-(4-fluorophenyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)piperidin-3-yl)carbamate 
• 1377432-87-5 tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-4-oxo-6-(4-(trifluoromethyl)phenyl)-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)piperidin-3-yl)carbamate 
• 1377432-86-4 tert-butyl ((3R)-1-(6-bromo-3-(2-cyanobenzyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)piperidin-3-yl)carbamate 
• 1377432-83-1 tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)piperidin-3-yl)carbamate 

Relevant articles and documents

Novel pyrrolopyrimidine analogues as potent dipeptidyl peptidase IV inhibitors based on pharmacokinetic property-driven optimization

We previously reported a highly potent DPP-IV inhibitor 6 with low in vivo efficacy. While trying to maintain consistent in vitro and in vivo biological activity, we initiated a pharmacokinetic property-driven optimization to improve the metabolic stability and permeability of inhibitor 6. A simple scaffold replacement of thienopyrimidine with pyrrolopyrimidine (21a) led to significantly improved metabolic stability (4% vs. 65% remaining). Further modification of the pyrrolopyrimidine scaffold to produce compound 21j resulted in much better oral bioavailability than 6. Importantly, compound 21j exhibits greater in vivo efficacy than does 6 and Alogliptin and is worthy of further development.