Potassium hydride → Dihydro-6-diethoxyphosphinyl-1-pyrindine-6-sulfonic acid, ethyl ester

HRID 1290652Notes

Reaction equation

[H-].[K+].[CH2:3]([O:5][P:6]([CH2:11][S:12]([O:15][CH2:16][CH3:17])(=[O:14])=[O:13])([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].Cl[CH2:19][C:20]1[C:25]([CH2:26]Cl)=[CH:24][CH:23]=[CH:22][N:21]=1>CS(C)=O>[CH2:3]([O:5][P:6]([O:8][CH2:9][CH3:10])([C:11]1([S:12]([O:15][CH2:16][CH3:17])(=[O:13])=[O:14])[CH:19]=[C:20]2[C:25]([CH:24]=[CH:23][CH2:22][NH:21]2)=[CH:26]1)=[O:7])[CH3:4]

Participants

Conditions

Temperature: 90 °C

Procedure

To an ice bath chilled solution of 35% potassium hydride in mineral oil (5.0 mmol) stirring under argon DMSO (7 ml) is added a solution of diethoxyphosphinyl methanesulfonic acid, ethyl ester (2.5 mmol) [prepared as described in J. C. Carretero, et. al., Tetrahedron, Vol. 43, pp. 5125-5134 (No. 21) 1987] in DMSO (5 ml). On completion of a dropwise addition, the resulting solution is stirred at room temperature for one hour. A solution of 2,3-bis(chloromethyl)pyridine (2.5 mmol) [prepared as described in K. Tsuda, et. al., Chem. Pharm. Bull., Vol.1, pp. 142, 1953] in DMSO (2 ml) is added slowly and the reaction mixture is then heated at 90° C. for 1 hour. After cooling, the reaction mixture is concentrated under reduced pressure and the desired product is purified by flash chromatography using a 5-15% isopropanol in methylene chloride gradient on silica gel.

Workup

customprepared
additionOn completion of a dropwise addition
stirringthe resulting solution is stirred at room temperature for one hour
temperatureAfter cooling
concentrationthe reaction mixture is concentrated under reduced pressure
customthe desired product is purified by flash chromatography

Sources & evidence

ORD record: ord-230599ab80d54575b37403df5149cc58
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753634

Reaction notes

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