HCID 11357648, compound → HCID 19827488, compound

HRID 1494290Notes

Reaction equation

Br[C:2](Br)=[CH:3][C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.C([Li])CCC.[CH3:15][CH:16]([CH3:25])[C:17]([C:19]1[CH:20]=[N:21][CH:22]=[N:23][CH:24]=1)=[O:18]>O1CCCC1>[OH:18][C:17]([C:19]1[CH:24]=[N:23][CH:22]=[N:21][CH:20]=1)([CH:16]([CH3:25])[CH3:15])[C:2]#[C:3][C:4]1[CH:8]=[CH:7][S:6][CH:5]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of the product of Stage (1) (0.22 g, 0.82 mmol) in dry tetrahydrofuran (15 ml) at --78° C. under nitrogen was slowly added n-butyl lithium (2.5 M in hexane; 0.8 ml, 2 mmol). After stirring for one hour at --78° C., the reaction mixture was allowed to warm to room temperature before 2-methyl-1-pyrimidin-5-ylpropan-1-one (0.2 g, 1.3 mmol) was added. After 20 minutes, the reaction was quenched by addition of water, and the product was extracted with ether (2×20ml). The combined organic extracts were washed with water, dried over sodium sulphate, filtered, and concentrated under reduced pressure to give an oil which was chromatographed on silica. Elution with ethyl acetate - hexane (1:1) gave the desired product as a yellow oil which solidified slowly on standing to give a solid of melting point 102-105° C.

Workup

custom-78° C.
additionwas added
waitAfter 20 minutes
customthe reaction was quenched by addition of water
extractionthe product was extracted with ether (2×20ml)
washThe combined organic extracts were washed with water
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give an oil which
customwas chromatographed on silica
washElution with ethyl acetate - hexane (1:1)

Sources & evidence

ORD record: ord-349a5e84e7be4c9bade9eb8c75a350fe
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05026418

Reaction notes

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