Benzophenone → HCID 13813644, compound

HRID 908536Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.CCCCCC.[Li]CCCC.[C:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[C:27]1([C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:2]2[CH:3]=[N:4][CH:5]=[N:6][CH:7]=2)[OH:26])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: -100 °C

Procedure

A solution of 5-bromopyrimidine (10 g, 0.063 mol) in a mixture of dry THF (150 mL) and hexane (50 mL) was cooled to −100° C. To this cooled solution was added n-BuLi (4 g, 21 mL, 0.062 mol) over a period of 30 min and stirred for another 30 min. A solution of benzophenone (11.5 g, 0.063 mol) in dry THF (50 mL) was added to this at the same temperature over a period of 30 min. The reaction mixture was warmed slowly to RT and allowed to stir another 1 h at RT. The reaction was quenched with cold water (200 mL), ethyl acetate was added and the organic layer was separated. The organic layer was dried, concentrated and the crude product was purified by column chromatography on silica gel (up-to 25% ethyl acetate in pet. ether) to give the product (8 g). TLC: Pet. ether/EtOAc, 1:1, Rf=0.3

Workup

temperatureThe reaction mixture was warmed slowly to RT
stirringto stir another 1 h at RT
customThe reaction was quenched with cold water (200 mL), ethyl acetate
additionwas added
customthe organic layer was separated
customThe organic layer was dried
concentrationconcentrated
customthe crude product was purified by column chromatography on silica gel (up-to 25% ethyl acetate in pet. ether)

Sources & evidence

ORD record: ord-d543dd9190c84f68be3fede8a1753172
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017620B2

Reaction notes

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