5-(Tributylstannyl)pyrimidine → 2-methoxy-7-(pyrimidin-5-yl)-9H-xanthen-9-one

HRID 455686Notes

Reaction equation

CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([Sn](CCCC)(CCCC)[C:40]1[CH:41]=[N:42][CH:43]=[N:44][CH:45]=1)CCC.Br[C:55]1[CH:68]=[CH:67][C:66]2[O:65][C:64]3[C:59](=[CH:60][C:61]([O:69][CH3:70])=[CH:62][CH:63]=3)[C:58](=[O:71])[C:57]=2[CH:56]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:70][O:69][C:61]1[CH:62]=[CH:63][C:64]2[O:65][C:66]3[C:57](=[CH:56][C:55]([C:40]4[CH:45]=[N:44][CH:43]=[N:42][CH:41]=4)=[CH:68][CH:67]=3)[C:58](=[O:71])[C:59]=2[CH:60]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A vial charged with Pd2(dba)3 (0.150 g, 0.164 mmol), XPhos (0.391 g, 0.819 mmol), 5-(tributylstannyl)pyrimidine (1.81 g, 4.92 mmol), 2-bromo-7-methoxy-9H-xanthen-9-one (1.000 g, 3.28 mmol) and dioxane (10 mL). The reaction mixture was evacuated and backfilled with nitrogen. The reaction mixture was heated to 100° C. overnight. The reaction mixture was cooled to RT and diluted with water and EtOAc. A grey solid precipitated out, which was filtered off. The solid was washed with EtOAc and water. The grey solid dried under reduced pressure to afford 2-methoxy-7-(pyrimidin-5-yl)-9H-xanthen-9-one) (0.600 g, 60.2% yield).

Workup

customThe reaction mixture was evacuated
temperatureThe reaction mixture was cooled to RT
additiondiluted with water and EtOAc
customA grey solid precipitated out
filtrationwhich was filtered off
washThe solid was washed with EtOAc and water
customThe grey solid dried under reduced pressure

Sources & evidence

ORD record: ord-7e96cc4aacfa414a9927a9d5c3bd74cc
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Reaction notes

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