1613509-49-1 | 2-Cyclobutyl-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5(3H,10H)-dione

Packsize	Purity	Availability	Price	Discounted Price
5mg	95%	in stock	$158.00	$110.00
10mg	95%	in stock	$258.00	$180.00
25mg	95%	in stock	$515.00	$360.00
50mg	95%	in stock	$829.00	$580.00
100mg	95%	in stock	$1,358.00	$950.00

Description

• Catalog Number: BG42269
• Chemical Name: 2-Cyclobutyl-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5(3H,10H)-dione
• CAS Number: 1613509-49-1
• Molecular Formula: C22H19N3O2
• Molecular Weight: 357.4052
• SMILES: O=c1n(c2ccccc2)c(nc2c1c(=O)c1ccccc1n2C)C1CCC1

Upstream Synthesis Route

To synthesize 2-Cyclobutyl-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5(3H,10H)-dione, one would likely begin with the construction of the pyrimidoquinoline core followed by subsequent functionalization to introduce the required substituents.

Step 1: Synthesis of Pyrimidoquinoline Core
- Begin with a Skraup synthesis involving quinoline as the starting material. Quinoline will be reacted with glycerol in the presence of sulfuric acid and an oxidizing agent, typically nitrobenzene, to yield a quinoline derivative.
- Perform a cyclization step where this quinoline derivative is treated with a suitable dihalide, followed by base-mediated closure of the pyrimidine ring.

Step 2: Installation of 3-Phenyl Group
- The 3-phenyl group can be introduced through a Friedel-Crafts acylation using phenylacetyl chloride in the presence of aluminum chloride (AlCl3) as a Lewis acid catalyst.

Step 3: Installation of 2-Cyclobutyl Group
- This might involve a nucleophilic substitution or a palladium-catalyzed cross-coupling reaction such as a Suzuki-Miyaura coupling with a cyclobutyl-boron compound.

Step 4: Introduction of 10-Methyl Group
- A 10-methyl group can be introduced via a selective alkylation at the proper position on the pyrimidoquinoline core. This will likely require the use of strong bases, such as LDA (Lithium diisopropylamide), and a methyl halide (CH3I or CH3Br).

Step 5: Formation of the Dione
- Oxidation of the pyrimidoquinoline to introduce the 4,5-dione. This could be accomplished by using an oxidizing agent such as NBS (N-Bromosuccinimide) in the presence of a radical initiator or through a careful controlled oxidation with an agent like dichlorodicyanobenzoquinone (DDQ).

Step 6: Purification
- Purify the synthesized compound through techniques such as recrystallization, chromatography, or preparative HPLC to achieve the desired purity of the final product.

Note that each synthetic step would likely require optimization of reaction conditions, including temperatures, solvents, and reaction times, along with thorough characterization of intermediates using techniques such as NMR, IR, MS, and potentially X-ray crystallography for solid-state structure elucidation. Safety precautions are paramount due to the reactive and potentially hazardous chemicals involved.