779326-74-8

Basic information

• Product Name: ethyl 4-hydroxy-5H-pyrrolo[3,2-d]pyriMidine-7-carboxylate
• Synonyms: 4,5-Dihydro-4-oxo-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid methyl ester
• CAS NO: 779326-74-8
• Molecular Formula: C₈H₇N₃O₃
• Molecular Weight: 207.18606
• EINECS: -0
• Mol File: 779326-74-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 220-222 °C
• Boiling Point: 497.8°C at 760 mmHg
• Flash Point: 254.9°C
• Appearance: /
• Density: 1.62g/cm³
• Vapor Pressure: 4.78E-10mmHg at 25°C
• Refractive Index: 1.71
• PKA: 13.44±0.20(Predicted)
• CAS DataBase Reference: ethyl 4-hydroxy-5H-pyrrolo[3,2-d]pyriMidine-7-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-hydroxy-5H-pyrrolo[3,2-d]pyriMidine-7-carboxylate(779326-74-8)
• EPA Substance Registry System: ethyl 4-hydroxy-5H-pyrrolo[3,2-d]pyriMidine-7-carboxylate(779326-74-8)

Safety Data

• Hazardous Substances Data: 779326-74-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H7N3O3/c1-14-8(13)4-2-9-6-5(4)10-3-11-7(6)12/h2-3,9H,1H3,(H,10,11,12)

Upstream product

• 3473-63-0 formamidine acetic acid 
• 180059-04-5 3-amino-1H-pyrrole-2,4-dicarboxylic acid dimethyl ester 
• 144918-37-6 1-cyano-1-ethoxycarbonyl-1-butene 
• 124-41-4 sodium methylate 
• 16115-80-3 dimethyl aminomalonate hydrochloride 
• 94-05-3 ethyl (ethoxymethylene)cyanoacetate 
• 36896-17-0 acetamidine acetate 

Downstream Products

• 1384950-69-9 5-methyl-7-(4-methanesulfonylphenyl)-4-(piperidin-4-yloxy)-5H-pyrrolo[3,2-d]pyrimidine 
• 364046-19-5 1S-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1-C-[(4-methyoxypyrrolo[3,2-d]pyrimidin-9-N-(benzyloxomethyl)-7-yl)]-1,4-imino-2,3-O-isopropylidine-D-ribitol 
• 402477-37-6 (2S,3S,4R,5R)-tert-butyl 2-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 917595-31-4 (6aR,8S,9S,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-[1,3,5,2,4]trioxadisilocino[7,6-b]pyrrole-7(8H)-carboxylate 
• 1163713-16-3 (6aR,8S,9R,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro[1,3,5,2,4]trioxadisilocino[7,6-d]pyrrole-7(8H)-carboxylate 
• 402477-42-3 (2S,3S,4R,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-3,4-dihydroxy-5-((trityloxy)methyl)pyrrolidine-1-carboxylate 
• 577978-31-5 (2S,3S,4R,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-3-hydroxy-4-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate 
• 402477-45-6 (2S,3S,4R,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate 
• 1163713-17-4 (2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate 
• 1026012-16-7 5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidine 
• 299916-62-4 7-N-benzyloxymethyl-9-bromo-9-deaza-6-O-methylhypoxanthine 
• 364046-18-4 1S-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1-C-[(4-methyoxypyrrolo[3,2-d]pyrimidin-9-N-(benzyloxomethyl)-7-yl)]-1,4-imino-2,3-O-isopropylidine-D-ribitol 
• 5655-01-6 9-deazahypoxanthine 

Relevant articles and documents

Infinite ladder-like chains organized into a three-dimensional zigzag supramolecular architecture in 9-deazahypoxanthine

The asymmetric unit of the title compound, C6H5N3O, consists of discrete molecules of 9-deazahypoxanthine [systematic name: 3H-pyrrolo[3,2-d]pyrimidin- 4(5H)-one]. The structure displays N - H ?O hydrogen bonding, connecting the molecules into centrosymmetric dimers. These dimers are then connected by N - H ?N hydrogen bonds into a ladder-like chain along the c axis. The secondary structure is stabilized by weak noncovalent contacts of the C - H ?O and C - H ?C types, as well as by π- π stacking interactions, which organize the structure into a zigzag architecture.

COMPOSITIONS AND METHODS FOR INHIBITING VIRAL POLYMERASE

Provided are compounds of Formula (I) as described herein. Compounds of Formula (I) are useful in methods of inhibiting viral RNA polymerase activity and viral replication. Also provided are pharmaceutical compositions comprising compounds of Formula (I), as well as methods of treating viral infections using compounds of Formula (I).

Development of a practical synthesis of a purine nucleoside phosphorylase inhibitor: BCX-4208

A practical synthesis of the purine nucleoside phosphorylase (PNP) inhibitor BCX-4208 (1) was accomplished in three telescoped steps. Mannich condensation of the 4-benzyloxy-9-deazahypoxanthine with (3R,4R)-3-hydroxy-4- (hydroxymethyl)pyrrolidine and formaldehyde followed by removal of the protecting group and crystallization furnished the desired product as a hydrochloride salt in 85% overall yield and 99.8% purity. A scalable synthesis of 9-deazahypoxanthine is also reported. 2009 American Chemical Society.