25940-35-6 | Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Packsize	Purity	Availability	Price	Discounted Price
1g	97%	in stock	$7.00	$5.00
5g	97%	in stock	$29.00	$21.00
10g	97%	in stock	$56.00	$40.00
25g	97%	in stock	$77.00	$54.00
50g	97%	in stock	$140.00	$98.00
100g	97%	in stock	$249.00	$174.00

Description

• Catalog Number: AB28305
• Chemical Name: Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid
• CAS Number: 25940-35-6
• Molecular Formula: C7H5N3O2
• Molecular Weight: 163.1335
• MDL Number: MFCD01975194
• SMILES: OC(=O)c1cnn2c1nccc2

Computed Properties

• Complexity: 197
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 12
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 1
• XLogP3: -0.1

Upstream Synthesis Route

The upstream synthesis route of Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid typically involves the construction of the pyrazole ring fused to the pyrimidine core. Here is a general synthesis pathway:

1. Start with a suitable pyrimidine derivative, such as 4,6-dichloropyrimidine, as the base compound which allows further functionalization at positions 4 and 6.

2. Introduce a nitro group at the 5-position of the pyrimidine ring through nitration reactions using nitric acid in an appropriate solvent such as acetic anhydride.

3. Use a Michael addition reaction to introduce the pyrazole moiety by reacting the nitropyrimidine with an appropriately substituted hydrazine (this could be phenylhydrazine or another substituted hydrazine depending on the desired substitution pattern of the final product).

4. The subsequent step involves the reduction of the nitro group to an amine using catalytic hydrogenation or other suitable reducing agents like tin chloride (SnCl2) or iron (Fe) and hydrochloric acid (HCl).

5. Cyclization of the resulting amino compound with ethoxymethylene malononitrile or similar β-keto ester derivatives in the presence of a base such as sodium ethoxide would form the pyrazolo[1,5-a]pyrimidine core.

6. Finally, introduce the carboxylic acid group at the 3-position, if it's not already present, through a Sandmeyer-type reaction, where the amine can be diazotized using sodium nitrite in acidic conditions, followed by a copper(I)-catalyzed carboxylation using carbon dioxide or a suitable carboxylating reagent.

Each step should be followed by adequate purification methods like recrystallization or column chromatography to ensure the desired purity of intermediates and the final product.