ChemicalBook CAS DataBase List 5-PyriMidinecarboxaldehyde, 2-chloro-4-(MethylaMino)-

5-PyriMidinecarboxaldehyde, 2-chloro-4-(MethylaMino)- synthesis

7synthesis methods

Product Name:5-PyriMidinecarboxaldehyde, 2-chloro-4-(MethylaMino)-
CAS Number:839708-50-8
Molecular formula:C6H6ClN3O
Molecular Weight:171.58

4-Pyrimidinamine, 2-chloro-5-ethenyl-N-methyl-

839708-49-5
0 suppliers
inquiry

5-PyriMidinecarboxaldehyde, 2-chloro-4-(MethylaMino)-

839708-50-8
33 suppliers
$200.00/100mg

Yield:839708-50-8 95%

Reaction Conditions:

Stage #1: (2-chloro-5-vinylpyrimidin-4-yl)methylaminewith ozone in methanol;chloroform at -78; for 0.55 h;
Stage #2: with dimethylsulfide in methanol;chloroform at -78 - 20;

Steps:

1

A solution of (2-chloro-5-vinyl-pyrimidin-4-yl)-methylamine (2.50 g, 14.7 mmol) in CHCl₃/MeOH (15 mL/15 mL) is bubbled by ozone for 30 minutes and then passed by a stream of argon for 3 minutes at -78 "C . The reaction mixture is allowed to warm up to room temperature and treated with dimethyl sulfide (3.24 mL, 44.1 mmol). The reaction mixture is concentrated under reduced pressure to give colorless oil that is purified by flash column chromatography (SiO₂, EtOAc/Hx = 1/3) over silica gel to give 2-chloro-4-methylamino- pyrimidine-5-carbaldehyde (2.40 g, 95%) as a white solid.

References:

WO2006/135824,2006,A1 Location in patent:Page/Page column 14