Sodium hydride → 4-[2-(4-Chlorophenyl)ethoxy]-5-methoxy-6-chloropyrimidine

HRID 342509Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Cl:15][C:16]1[C:21]([O:22][CH3:23])=[C:20](Cl)[N:19]=[CH:18][N:17]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:20]2[C:21]([O:22][CH3:23])=[C:16]([Cl:15])[N:17]=[CH:18][N:19]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

2.40 g (15.2 mmol) of 2-(4-chlorophenyl)ethanol were added dropwise at 40° C. to a suspension of 680 mg (22.7 mmol) of sodium hydride (80% suspension in oil) in 40 ml of dry tetrahydrofuran, and the mixture was stirred until the evolution of hydrogen had ceased. The mixture was then allowed to cool to room temperature, whereupon 2.7 g (15.2 mmol) of 4,6-dichloro-5-methoxypyrimidine (Monatshefte Chem. 96, 1661 (1965) were added in portions. The mixture was stirred for 1 hour at room temperature and for 4 hours at 40° C. For work-up, the reaction mixture was poured into saturated ammonium chloride solution and extracted with diethyl ether. The combined organic phase was dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel using n-heptane/ethyl acetate (4:1). 4.0 g (88% of theory) of 4-[2-(4-chlorophenyl)ethoxy]-5-methoxy-6-chloropyrimidine was obtained in the form of a viscous oil which crystallized slowly upon drying (melting point 70°-71° C.).

Workup

addition96, 1661 (1965) were added in portions
extractionextracted with diethyl ether
dry with materialThe combined organic phase was dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-86d8a7d930f8469f9f096ad4edc162e3
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859020

Reaction notes

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