3680-71-5

Basic information

• Product Name: Pyrrolo[2,3-d]pyrimidin-4-ol
• Synonyms: 1,7-DIHYDRO-4H-PYRROLO[3,2-D]PYRIMIDIN-4-ONE;4-HYDROXYPYRROLO[2,3-D]PYRIMIDINE;3H-PYRROLO[2,3-D]PYRIMIDIN-4(7H)-ONE;7-DEAZAHYPOXANTHINE;7H-PYRROLO[2,3-D]PYRIMIDIN-4-OL;7-DEAZA-6-HYDROXY PURINE;1,7-dihydro-4h-pyrrolo(2,3-d)pyrimidin-4-one;3-d)pyrimidin-4-one,1,7-dihydro-4h-pyrrolo(
• CAS NO: 3680-71-5
• Molecular Formula: C₆H₅N₃O
• Molecular Weight: 135.12
• EINECS: 1592732-453-0
• Product Categories: PYRIMIDINE;Nucleotides and Nucleosides;Bases & Related Reagents;Intermediates;Nucleotides
• Mol File: 3680-71-5.mol
• Article Data: 27

Chemical Properties

• Melting Point: 345-348°C
• Boiling Point: 239.894 °C
• Flash Point: 473.052 °C at 760 mmHg
• Appearance: Brown/Solid
• Density: 1.62 g/cm³
• Vapor Pressure: 2.22E-06mmHg at 25°C
• Refractive Index: 1.784
• Storage Temp.: -20°C Freezer
• Solubility: Soluble in dimethyl sulfoxide.
• PKA: 11.99±0.20(Predicted)
• Sensitive: Moisture & Light Sensitive
• CAS DataBase Reference: Pyrrolo[2,3-d]pyrimidin-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolo[2,3-d]pyrimidin-4-ol(3680-71-5)
• EPA Substance Registry System: Pyrrolo[2,3-d]pyrimidin-4-ol(3680-71-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• RTECS: UY9440000
• HazardClass: IRRITANT
• Hazardous Substances Data: 3680-71-5(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Crystalline Solid

Uses

Different sources of media describe the Uses of 3680-71-5 differently. You can refer to the following data:
1. Xanthine oxidase-activated prodrug of thymidine phosphorylase inhibitor
2. It is used as pharmaceutical intermediate. Methylated 7-Deazahypoxanthines is used as regiochemical probes of xanthine oxidase.

InChI:InChI=1/C6H5N3O/c10-6-4-1-2-7-5(4)8-3-9-6/h1-3H,(H2,7,8,9,10)

Upstream product

• 7400-06-8 4-amino-6-hydroxy-5-(2,2-diethoxyethyl)pyrimidine 
• 7400-05-7 6-amino-5-(2,2-diethoxy)-2-mercaptopyrimidine-4-ol 
• 67831-84-9 2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 52133-67-2 ethyl 2-cyano-4,4-diethoxybutyrate 
• 7400-05-7 6-amino-5-(2,2-diethoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 
• 67831-84-9 2-thioxo-1,2,3,7-tetrahydro-pyrrolo[2,3-d]pyrimidin-4-one 
• 107-20-0 2-chloroethanal 
• 1193-22-2 6-amino-4-hydroxy-[3,4-d]pyrimidine 
• 17157-48-1 bromoacetaldehyde 
• 463-52-5 formamidine 
• 67831-84-9 2-mercapto-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine 
• 773076-83-8 2-cyano-4,4-dimethoxybutyric acid ethyl ester 
• 3473-63-0 formamidine acetic acid 
• 7400-06-8 6-amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol 

Downstream Products

• 1421-27-8 3,7-Dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-thion 
• 81965-15-3 3,7-Dihydro-3-methyl-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 39929-79-8 7-deazaxanthine 
• 271-70-5 7H-pyrrolo[2,3-d]pyrimidine 
• 7781-10-4 4-Chlor-7-methyl-7H-pyrrolo<2,3-d>pyrimidin 
• 94581-94-9 4-(piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 346599-63-1 4-chloro-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one 
• 186519-85-7 (3-ethynyl-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine 
• 346600-33-7 (3-chloro-4-fluoro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine 
• 865364-20-1 (4-chloro-2-fluoro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine 
• 346600-34-8 (3-chloro-4-fluoro-phenyl)-(7-methyl-7H-pyrrolo [2,3-d]pyrimidin-4-yl)-amine 
• 865364-80-3 4-(3-ethynyl-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one 
• 865364-29-0 4-(4-chloro-2-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one 

Relevant articles and documents

Preparation method of prodrug intermediate of thymidine phosphorylase inhibitor

The invention relates to the field of preparation of prodrug intermediates of thymidine phosphorylase inhibitors, and discloses a preparation method of a prodrug intermediate of a thymidine phosphorylase inhibitor. The method comprises the following steps: (1) adding ethyl cyanoacetate into a mixed alcoholic-alkaline solution of thiourea, carrying out reflux reaction for 5-6 hours, performing cooling, crystallizing, filtering, and washing with an ethanol/dioxane mixed solution; (2) mixing pyridine with ammonia water, adding Raney nickel, ZnSO4 and the product obtained in the step (1), heating and reacting at 65-75 DEG C for 7-8 hours, performing filtering while the product is hot, and performing cooling and crystallizing, filtering and washing; and (3) adding the product obtained in the step (2) into a mixed alkali solution, slowly adding 2-bromoacetaldehyde at 45-55 DEG C, reacting for 4-5 hours, and performing cooling, crystallizing, filtering, washing and drying. According to the preparation method disclosed by the invention, the total yield of the prodrug intermediate 4-hydroxypyrrolo[2, 3-d] pyrimidine of the thymidine phosphorylase inhibitor is improved.

Synthetic method of medical intermediate 4-chloropyrrolopyrimidine

The invention discloses a synthetic method of a medical intermediate, i.e., 4-chloropyrrolopyrimidine. The synthetic method comprises the following steps: with 4-hydroxypyrrolo[2, 3-d]pyrimidine as areaction substrate and a mixed solution of NMP/methylbenzene as a solvent; adding 2.0 to 4.0 equivalents of 1,2,3-trichloropropane into a reaction kettle, carrying out a refluxing and stirring reaction for 4-5 h at 100-120 DEG C in a chlorine environment, carrying out vucummizing at 160-180 DEG C to evaporate excessive solvent so as to obtain an oily substance, starting stirring, adding a sodium hydroxide solution with a concentration of 0.5-1mol/L into the oily substance, and performing filtering and drying to obtain the 4-chloropyrrolopyrimidine product. POCl3 is replaced by using the novelmethod, so the problems of quenching danger and low working efficiency of conventional synthesis methods are solved.

Synthetic method of 4-chloropyrrolopyrimidine

The invention relates to a synthetic method of 4-chloropyrrolopyrimidine. The synthetic method takes ethyl cyanoacetate, bromoacetaldehyde diethyl acetal, thiourea, sodium ethoxide and hydrogen peroxide as raw materials and takes DMF, ethanol, water and phosphorous oxychloride as solvents to obtain the target product 4-chloropyrrolopyrimidine through four steps of reactions. The method improves amethod of removing a mercapto group in a third step. The mercapto group is first oxidized to sulfinic acid by using the hydrogen peroxide and then is removed under acidic conditions. The method is mild in reaction conditions, safe in operation and high in yield, is environmentally friendly, and is suitable for industrial production.