Triethylamine → (E)-6-[3-(4-cyanophenoxy)-3-methyl-1-butenyl]pyrimidine 1-oxide

HRID 1073955Notes

Reaction equation

CS(Cl)(=O)=O.[C:6]([C:8]1[CH:27]=[CH:26][C:11]([O:12][C:13]([CH3:25])([CH3:24])[CH:14](O)[CH2:15][C:16]2[N+:21]([O-:22])=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)#[N:7].C(N(CC)CC)C>ClCCl>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]([CH3:24])([CH3:25])/[CH:14]=[CH:15]/[C:16]2[N+:21]([O-:22])=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:26][CH:27]=1)#[N:7]

Participants

Conditions

Temperature: 20 °C

Procedure

0.23 g of methanesulphonyl chloride was added to a solution of 0.59 g of 6-[3-(4-cyanophenoxy)-2-hydroxy- 3-methylbutyl]pyrimidine 1-oxide and 0.2 g of triethylamine in 10 ml of dichloromethane. The mixture was stirred at 20° C. for 2 hours and then a further 0.46 g of methanesulphonyl chloride and 0.4 g of triethylamine were added. After 2 hours a further 0.6 g of triethylamine was added and the mixture was stirred for 1.5 hours. The mixture was then washed with water and evaporated. The residue was chromatographed on silica gel using ethyl acetate for the elution to give 0.25 g of (E)-6-[3-(4-cyanophenoxy)-3-methyl-1-butenyl]pyrimidine 1-oxide in the form of a pale yellow solid of melting point 101°-102° C.

Workup

stirringthe mixture was stirred for 1.5 hours
washThe mixture was then washed with water
customevaporated
customThe residue was chromatographed on silica gel
washfor the elution

Sources & evidence

ORD record: ord-9011c3d493cc4d588545b891e0624c52
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04971982

Reaction notes

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