1003845-08-6 | 2-Chloropyrimidine-5-boronic acid pinacol ester

Packsize	Purity	Availability	Price	Discounted Price
1g	97%	in stock	$11.00	$8.00
5g	97%	in stock	$20.00	$14.00
10g	97%	in stock	$39.00	$28.00
25g	97%	in stock	$77.00	$54.00

Description

• Catalog Number: AA02208
• Chemical Name: 2-Chloropyrimidine-5-boronic acid pinacol ester
• CAS Number: 1003845-08-6
• Molecular Formula: C10H14BClN2O2
• Molecular Weight: 240.4944
• MDL Number: MFCD18837563
• SMILES: CC1(C)OB(OC1(C)C)c1cnc(nc1)Cl

Computed Properties

• Complexity: 252
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 16
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1

Upstream Synthesis Route

The synthesis of 2-Chloropyrimidine-5-boronic acid pinacol ester typically involves the following steps:

1. **Synthesis of 2-Chloropyrimidine**: This can be achieved by chlorination of pyrimidine using an appropriate chlorinating agent like N-chlorosuccinimide (NCS) or phosphorus oxychloride (POCl3).

2. **Borylation at the 5-Position**: The chloropyrimidine is then subjected to a borylation reaction to introduce the boronic acid functionality. This can be done using a boron source such as bis(pinacolato)diboron (B2pin2) in the presence of a palladium catalyst (e.g., Pd(PPh3)4) and a base like potassium acetate (KOAc).

3. **Isolation and Purification**: The reaction mixture from the borylation will typically be worked up by aqueous washes, organic extraction, and chromatographic separation to isolate the 2-Chloropyrimidine-5-boronic acid.

4. **Esterification**: Finally, the isolated boronic acid is reacted with pinacol in the presence of a condensing agent like dicyclohexylcarbodiimide (DCC) to form the pinacol ester.

5. **Further Purification**: The crude product can be purified, often by recrystallization or further chromatography, to obtain the pure 2-Chloropyrimidine-5-boronic acid pinacol ester.

Each step must be closely monitored and controlled to ensure the purity of intermediates and final product, considering that by-products and incomplete reactions can lead to side products. Fine-tuning of conditions such as temperature, reaction time, and stoichiometry is also imperative for achieving high yields and selectivity.