Pyrrolo[2,3-d]pyrimidin-4-ol

Base Information

• Chemical Name: Pyrrolo[2,3-d]pyrimidin-4-ol
• CAS No.: 3680-71-5
• Molecular Formula: C6H5N3O
• Molecular Weight: 135.125
• Hs Code.: 29335990
• Mol file: 3680-71-5.mol

Synonyms:4H-Pyrrolo[2,3-d]pyrimidin-4-one,1,7-dihydro- (9CI);7H-Pyrrolo[2,3-d]pyrimidin-4-ol (6CI,7CI,8CI);7-Deazahypoxanthine;NSC 124164;NSC 59251;

Chemical Property of Pyrrolo[2,3-d]pyrimidin-4-ol

Chemical Property:

• Appearance/Colour: colourless crystalline solid
• Vapor Pressure: 2.22E-06mmHg at 25°C
• Melting Point: 345-348 °C
• Refractive Index: 1.784
• Boiling Point: 239.894 °C
• PKA: 11.99±0.20(Predicted)
• Flash Point: 473.052 °C at 760 mmHg
• PSA: 61.54000
• Density: 1.62 g/cm³
• LogP: 0.25120
• Storage Temp.: -20°C Freezer
• Sensitive.: Moisture & Light Sensitive
• Solubility.: Soluble in dimethyl sulfoxide.

Purity/Quality:

99% ^*data from raw suppliers

7-Deazahypoxanthine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Xanthine oxidase-activated prodrug of thymidine phosphorylase inhibitor It is used as pharmaceutical intermediate. Methylated 7-Deazahypoxanthines is used as regiochemical probes of xanthine oxidase.

Technology Process of Pyrrolo[2,3-d]pyrimidin-4-ol

There total 27 articles about Pyrrolo[2,3-d]pyrimidin-4-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

6-amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol (7400-06-8) → Allopurinol (3680-71-5)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 2.5h;

DOI:10.1016/j.bmc.2012.08.050

Reference yield: 86.0%

4-amino-6-hydroxy-5-(2,2-diethoxyethyl)pyrimidine (7400-06-8) → 7-deazahypoxanthine (3680-71-5)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 1h;

Reference yield: 85.2%

2-cyano-3-(1,3-dioxolan-2-yl)propionic acid ethyl ester + formamidine acetic acid (3473-63-0) → Allopurinol (3680-71-5)

Guidance literature:

formamidine acetic acid; With sodium; In ethanol; at 20 ℃; for 1h; Inert atmosphere; Cooling with ice;

2-cyano-3-(1,3-dioxolan-2-yl)propionic acid ethyl ester; In ethanol; at 80 ℃; for 18h; Temperature; Solvent;

upstream raw materials:

4-amino-6-hydroxy-5-(2,2-diethoxyethyl)pyrimidine

6-amino-5-(2,2-diethoxy)-2-mercaptopyrimidine-4-ol

2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

ethyl 2-cyano-4,4-diethoxybutyrate

Downstream raw materials:

3,7-Dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-thion

3,7-Dihydro-3-methyl-4H-pyrrolo<2,3-d>pyrimidin-4-on

7-Methyl-7H-pyrrolo<2,3-d>pyrimidin

7,7'-Methylendi(7H-pyrrolo<2,3-d>pyrimidin)

Refernces

• 1、 -. "Production process 4 -chloropyrrolo [2, 3 - d] pyrimidine". Paragraph 0108; 0112. . Retrieved 2021/10/27.
• 2、 -. "Synthetic method of medical intermediate 4-chloropyrrolopyrimidine". Paragraph 0020; 0024-0025. . Retrieved 2020/02/14.