1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion

Base Information

• Chemical Name: 1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion
• CAS No.: 65996-50-1
• Molecular Formula: C6H5N3O2
• Molecular Weight: 151.125
• Hs Code.: 2933990090
• Mol file: 65996-50-1.mol

Synonyms:5H-Pyrrolo[3,2-d]pyrimidine-2,4-diol;

Chemical Property of 1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion

Chemical Property:

• Vapor Pressure: 2.35E-15mmHg at 25°C
• Melting Point: >360 °C(Solv: water (7732-18-5))
• Refractive Index: 1.624
• Boiling Point: 607.6 °C at 760 mmHg
• PKA: 11.32±0.20(Predicted)
• Flash Point: 321.2 °C
• PSA: 81.51000
• Density: 1.516 g/cm³
• LogP: -0.45550
• Storage Temp.: 2-8°C

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion is used for the preparation of pyrazolopyrimidine derivatives or analogs thereof as CCR4 function modulators.

Technology Process of 1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion

There total 10 articles about 1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion 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: 97.0%

(E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4-diol (116705-41-0) → 2,4-dihydroxy-5H-pyrrolo[3,2-d]pyrimidine (65996-50-1)

Guidance literature:

With acetic acid; zinc; at 0 - 100 ℃;

DOI:10.1021/ja9064359

Reference yield: 89.8%

(E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione (116705-41-0) → 2,4-Dioxo-1,2,3,4-tetrahydropyrrolo<3,2-d>pyrimidine (65996-50-1)

Guidance literature:

With acetic acid; zinc;

DOI:10.1016/j.bmc.2015.06.025

Reference yield: 82.46%

5-Nitro-2,4-dioxo-6-(β-dimethylaminovinyl)-1,2,3,4-tetrahydropyrimidine (116705-41-0,114684-92-3) → 2,4-Dioxo-1,2,3,4-tetrahydropyrrolo<3,2-d>pyrimidine (65996-50-1)

Guidance literature:

With acetic acid; zinc; at 70 - 80 ℃; for 1h;

DOI:10.1007/BF00758443

upstream raw materials:

5-Nitro-2,4-dioxo-6-(β-dimethylaminovinyl)-1,2,3,4-tetrahydropyrimidine

allyltriphenylphosphonium bromide

5-nitro-6-methyluracil

ethyl 3-ureido-1H-pyrrole-2-carboxylate

Downstream raw materials:

tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-4-oxo-7-(pyridin-3-yl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-3-yl)carbamate

tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-4-oxo-7-(pyridin-4-yl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-3-yl)carbamate

tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-4-oxo-7-(thiophen-3-yl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-3-yl)carbamate

2-((2-((R)-3-aminopiperidin-1-yl)-7-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-3-yl)methyl)benzonitrile

Refernces

• 1、 Cawrse, Brian M.,Robinson, Nia'mani M.,Lee, Nina C.,Wilson, Gerald M.,Seley-Radtke, Katherine L.. "Structural and Biological Investigations for a Series of N-5 Substituted Pyrrolo[3,2-d]pyrimidines as Potential Anti-Cancer Therapeutics". . . Retrieved 2019/08/01.
• 2、 -. "Pyrrolopyrimidine ketone compound and preparation method and application thereof". Paragraph 0114; 0116; 0117; 0124; 0125; 0126. . Retrieved 2017/07/21.