188062-43-3

Basic information

• Product Name: ethyl 2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidine-6-carboxylate
• CAS NO: 188062-43-3
• Molecular Formula: C₉H₁₀N₄O₃
• Molecular Weight: 222.2007
• Mol File: 188062-43-3.mol

Chemical Properties

• Boiling Point: 517.234°C at 760 mmHg
• Flash Point: 266.614°C
• Density: 1.688g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.737
• CAS DataBase Reference: ethyl 2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidine-6-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidine-6-carboxylate(188062-43-3)
• EPA Substance Registry System: ethyl 2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidine-6-carboxylate(188062-43-3)

Safety Data

• Hazardous Substances Data: 188062-43-3(Hazardous Substances Data)

Upstream product

• 100643-27-4 2,6-diamino-3H-pyrimidin-4-one 
• 70-23-5 ethyl Bromopyruvate 
• 134288-26-9 3-bromo-2-hydroxyimino-propionic acid ethyl ester 
• 73472-94-3 ethyl 3-bromo-2-(hydroxyimino)propanoate 
• 188062-38-6 3-(2,4-Diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-2-[(Z)-hydroxyimino]-propionic acid ethyl ester 

Relevant articles and documents

Synthesis of potential inhibitors of GTP-cyclohydrolase I: An efficient synthesis of 8-substituted 7-deazaguanines

A novel two step synthesis of 8-substituted 7-deazaguanines is developed and involves the regioselective alkylation of pyrimidinones 1a and 1b with nitrosoalkenes derived from α-halo oximes followed by transoximation to give the 7-deazaguanines 6a-d in 41

Improved conditions for a direct and regioselective synthesis of 8-carboxyethyl-7-deazaguanine

As deazaguanines have a broad range of applications, from medicinal research to supramolecular assemblies, simple pathways to functionalizable versions of this heterocycle are of noted importance. The cyclization reaction leading to deazaguanines is known to also lead to a furano-isomer, exclusively in some cases. 8-Carboxyethyl-7-deazaguanine (1) had failed to form through the typical cyclization conditions and previously required a considerably more longwinded synthetic approach to form over the furo-isomer (2). We report herein a more direct, simplified approach to 1 by iterative modification of the cyclization reaction conditions, which resulted in a complete reversal of regiochemistry in favor of the desired deazaguanine.

SUBSTITUTED PYRROLO[2,3-D]DIPYRIMIDINES FOR SELECTIVELY TARGETING TUMOR CELLS WITH FR-ALPHA AND FR-BETA TYPE RECEPTORS

Pyrrolo[2,3-d]pyrimidine derivatives, and pharmaceutical acceptable salts thereof, useful in therapeutically treating patients with cancer are disclosed. These compounds selectively target folate receptors (FR) of cancerous tumor cells and inhibit purine synthesis and hence, DNA synthesis.

Specific inhibitors in vitamin biosynthesis. Part 10. Synthesis of 7- and 8-substituted 7-deazaguanines

Versatile syntheses of 7- and 8-substituted 7-deazaguanines including N-alkyl derivatives have been developed by identifying selective annulation reactions with 2,6-diaminopyrimidin-4(3H)-one as substrate and β-halocarbonyl compounds as electrophiles. A new synthesis of 8-substituted 7-deazaguanines using nitrosoalkenes as electrophiles is described. With some combinations of reactants, furo[2,3-d]pyrimidines are significant products in place of or in addition to the required 7-deazaguanines [pyrrolo[2,3-d]-pyrimidin-4(3H)-ones]. When 2,4-diamino-6-chloropyrimidine was used as a substrate, imidazo-pyrimidines were produced.