ChemicalBook CAS DataBase List 4,6-dichloropyrimidine-5-carbonitrile

4,6-dichloropyrimidine-5-carbonitrile synthesis

6synthesis methods

Product Name:4,6-dichloropyrimidine-5-carbonitrile
CAS Number:5305-45-3
Molecular formula:C5HCl2N3
Molecular Weight:173.99

4,6-Dichloro-5-pyrimidinecarbaldehyde oxime (8 g) was dissolved in CHCl3 (40 mL) and treated with SOCl2 (6 mL) for 2 h at rt. The solvent was removed and the residue was dissolved in DCM (5 mL). The resulting solid was filtered and washed with DCM (5 mL). The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography using DCM-hexane (3:1) to give 4,6-dichloro-5-pyrimidinecarbonitrile. White solid.

7660-48-2
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5305-45-3
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Yield:5305-45-3 91%

Reaction Conditions:

with thionyl chloride at 0 - 20; for 3.5 h;

Steps:

12 Compound A91; 4- [4- (3-ISOPROPYL- [1, 2,4] oxadiazol-5-yl)-piperidin-1-yl]-6- (4-methanesulfonyl-phenoxy)- pyrimidine-5-carbonitrile ;

The starting material, 4, 6-DICHLORO-PYRIMIDINE-5-CARBONITRILE, used in the preparation of Compound A91 was prepared in the following manner: To a solution of 5-fomyl-4, 6- dichloropyrimidine (3.6 g, 20.3 mmol) in EtOAc (50 ML), was added a solution OF NH20H-HC1 (1.41 g, 20.3 mmol) in H2O (30 ML) followed by AcONa (1.67 g, 20.3 mmol) at rt. After stirring for 2h, the reaction was washed with H20 (50 ML, two times) and dried over MgS04. The EtOAc was concentrated under vacuum to afford the crude IMINOHYDROXY compound (3.51 g, 90.2%). The crude compound was used for next step without further purification. The IMINOHYDROXY compound (3.51 g, 18.3 mmol) was dissolved in SOC12 (20 ML) at 0 °C and stirred for 30 min. The reaction was warmed to rt and maintained for 3h. The reaction was poured into H20 (100 g) portionwise and stirred for 30 min. The precipitate was filtered, washed with H2O (100 mL) and dried under vacuum to afford 4, 6-DICHLORO-PYRIRNIDINE-5-CARBONITRILE (2.99g, 91%).'H-NMR (DMSO-d6) : 8.53 ppm; LCMS: not detectable.

References:

WO2004/65380,2004,A1 Location in patent:Page 151-152

911461-47-7 Synthesis