1003845-06-4 | 2-Chloropyrimidine-5-boronic acid

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$13.00	$9.00
5g	95%	in stock	$25.00	$18.00
10g	95%	in stock	$45.00	$32.00
25g	95%	in stock	$57.00	$40.00
50g	95%	in stock	$96.00	$67.00
100g	95%	in stock	$192.00	$134.00
250g	95%	in stock	$469.00	$328.00

Description

• Catalog Number: AA02167
• Chemical Name: 2-Chloropyrimidine-5-boronic acid
• CAS Number: 1003845-06-4
• Molecular Formula: C4H4BClN2O2
• Molecular Weight: 158.3508
• MDL Number: MFCD08063113
• SMILES: OB(c1cnc(nc1)Cl)O

Computed Properties

• Complexity: 107
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 1

Upstream Synthesis Route

To synthesize 2-Chloropyrimidine-5-boronic acid, one could follow these steps:

1. Start with 2,4,6-trichloropyrimidine as the raw material.
2. Perform a lithiation reaction by treating 2,4,6-trichloropyrimidine with tert-butyllithium (t-BuLi) in an inert atmosphere (e.g., argon) at low temperatures to selectively lithiate the 5-position of the pyrimidine ring.
3. Quench the resulting lithiated intermediate with a boronic acid ester like trimethyl borate (B(OCH3)3) to introduce the boronic acid functionality at the 5-position, forming 2,4,6-trichloropyrimidine-5-boronic acid ester.
4. Hydrolyze the ester group to the corresponding boronic acid using aqueous acid, for example, concentrated hydrochloric acid (HCl).
5. Conduct a halogen exchange reaction (Halex process) on the remaining 4-chlorine by treating with a nucleophile, such as potassium fluoride (KF), to replace the chloro group with a fluoro group, obtaining 2-chloro-5-fluoropyrimidine-5-boronic acid.
6. Finally, the fluorine atom can be substituted back to chlorine by reaction with chlorine gas or a chlorine-releasing reagent, leading to the targeted 2-chloropyrimidine-5-boronic acid.

Throughout this synthesis, careful controlling of reaction temperatures, stoichiometry, and purification techniques, such as chromatography, are required to ensure selectively and high yields.