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Home > Product > Heterocyclic Organic Compounds > 2-Aminopyrimidine-5-boronic acid,pinacol ester

2-Aminopyrimidine-5-boronic acid,pinacol ester | CAS Number: 402960-38-7

Catalog Number
ACM402960387
Product Name
2-Aminopyrimidine-5-boronic acid,pinacol ester
Structure
CAS Number
402960-38-7
IUPAC Name
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine
Synonyms
2-AMINO-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIMIDINE;2-AMINOPYRIMIDINE-5-BORONIC ACID, PINACOL ESTER;5-METHOXYTHIOPHENE-2-BORONIC ACID;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine;(2-Aminopyrimidin-5-yl)boronic acid pinaco
Molecular Weight
221.06
Exact Mass
221.13400
Molecular Formula
C10H16BN3O2
Boiling Point
394.8ºC at 760 mmHg
Melting Point
209-211ºC
Flash Point
192.6ºC
Density
1.13 g/cm3
Purity
96%
SMILES
B1(OC(C(O1)(C)C)(C)C)C2=CN=C(N=C2)N
InChIKey
BPQVMIDUTRJYSC-UHFFFAOYSA-N
H-Bond Donor
1
H-Bond Acceptor
5
Safty Description
26-36/39
Hazard Statements
Xi
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1Synthesis of C-4 Substituted Amido Nicotine Derivatives via Copper(I)- and (II)-Catalyzed Cross-Coupling Reactions.

Zhu J1, Enamorado MF1, Comins DL1.

J Org Chem. 2016 Nov 18;81(22):11529-11534. Epub 2016 Nov 1.

The syntheses of seven novel amido nicotine derivatives 12-18 from (S)-nicotine are presented. (S)-Nicotine and (S)-6-chloronicotine derivatives were cross-coupled with the corresponding amides 6-10 at the C-4 position of the pyridine ring via copper(I)-mediated reactions. Derivatives 16-18 were also obtained via copper(II)-mediated reactions from (S)-nicotine containing a C-4 boronic acid pinacol ester group. The optimization of reaction conditions for both routes provided a useful method for preparing C-4 amide-containing nicotine analogs.

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