9-(1,3-Dioxolan-2-ylMethyl)-3,9-dihydro-1,3-diMethyl-1H-purine-2,6-dione

Base Information

• Chemical Name: 9-(1,3-Dioxolan-2-ylMethyl)-3,9-dihydro-1,3-diMethyl-1H-purine-2,6-dione
• CAS No.: 1174289-18-9
• Molecular Formula: C₁₁H₁₄N₄O₄
• Molecular Weight: 266.257
• Mol file: 1174289-18-9.mol

Synonyms:

Chemical Property of 9-(1,3-Dioxolan-2-ylMethyl)-3,9-dihydro-1,3-diMethyl-1H-purine-2,6-dione

Chemical Property:

• Boiling Point: 505.2±53.0 °C(Predicted)
• PKA: 0.61±0.70(Predicted)
• Density: 1.59±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

9-?(1,?3-?Dioxolan-?2-?ylmethyl)?-?3,?9-?dihydro-?1,?3-?dimethyl-1H-?purine-?2,?6-?dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 9-(1,3-Dioxolan-2-ylmethyl)-3,9-dihydro-1,3-dimethyl-1H-purine-2,6-dione is an isomer impurity in the synthesis of Doxofylline (D557100), a xanthine molecule that appears to be both bronchodilator and anti-inflammatory with an improved therapeutic window over conventional xanthines such as Theophylline and the evidence supporting the effects of Doxofylline in the treatment of lung diseases.

Technology Process of 9-(1,3-Dioxolan-2-ylMethyl)-3,9-dihydro-1,3-diMethyl-1H-purine-2,6-dione

There total 6 articles about 9-(1,3-Dioxolan-2-ylMethyl)-3,9-dihydro-1,3-diMethyl-1H-purine-2,6-dione 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: 51.6%

1,3-dimethyl-9-[(2,2-dimethoxy)ethylamino]-3,9-dihydro-1H-purine-2,6-dione + ethylene glycol (107-21-1) → 1,3-dimethyl-9-[(1,3-dioxolan-2-yl)methyl]-3,9-dihydro-1H-purine-2,6-dione (1174289-18-9)

Guidance literature:

With toluene-4-sulfonic acid; at 120 ℃; for 10h; Temperature; Flow reactor;

Reference yield:

6-bromo-1,3-dimethyluracil (21428-17-1) → 1,3-dimethyl-9-[(1,3-dioxolan-2-yl)methyl]-3,9-dihydro-1H-purine-2,6-dione (1174289-18-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 4-methyl-morpholine / isopropyl alcohol / 7 h / 30 °C / Reflux

2.1: sodium nitrite / water

2.2: 3 h / 100 °C

3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 h / 20 °C / 760.05 Torr

4.1: toluene-4-sulfonic acid / 1.5 h / 20 - 85 °C

5.1: toluene-4-sulfonic acid / 10 h / 120 °C / Flow reactor

With 4-methyl-morpholine; palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid; sodium nitrite; In methanol; water; isopropyl alcohol;

Reference yield:

1,3-Dimethyl-6-chlorouracil (6972-27-6) → 1,3-dimethyl-9-[(1,3-dioxolan-2-yl)methyl]-3,9-dihydro-1H-purine-2,6-dione (1174289-18-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium carbonate / isopropyl alcohol / 7 h / Reflux

2.1: sodium nitrite / water

2.2: 3 h / 100 °C

3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 h / 20 °C / 760.05 Torr

4.1: toluene-4-sulfonic acid / 1.5 h / 20 - 85 °C

5.1: toluene-4-sulfonic acid / 10 h / 120 °C / Flow reactor

With palladium 10% on activated carbon; hydrogen; sodium carbonate; toluene-4-sulfonic acid; sodium nitrite; In methanol; water; isopropyl alcohol;

upstream raw materials:

ethylene glycol

6-bromo-1,3-dimethyluracil

1,3-Dimethyl-6-chlorouracil

Refernces