Stannane, tributyl(1-ethoxyethenyl)- → 8-acetyl-3-methyl-2-(methylthio)quinazolin-4(3H)-one

HRID 1056092Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([S:12][CH3:13])[N:8]([CH3:14])[C:7]2=[O:15].C([Sn](CCCC)(CCCC)[C:21]([O:23]CC)=[CH2:22])CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:21]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([S:12][CH3:13])[N:8]([CH3:14])[C:7]2=[O:15])(=[O:23])[CH3:22]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 8-bromo-3-methyl-2-(methylthio)quinazolin-4(3H)-one (500 mg, 1.753 mmol), tributyl(1-ethoxyvinyl)stannane (Synthonix, Wake Forest, N.C.; 0.652 mL, 1.929 mmol), and Pd(PPh3)4 (81 mg, 0.070 mmol) in toluene (9.0 mL) was stirred under argon at 100° C. for 19 h, then at 110° C. for 1 d. The reaction was cooled to 25° C. and concentrated onto silica gel. Chromatographic purification (silica gel, 0-50% EtOAc/Hexanes) furnished 8-acetyl-3-methyl-2-(methylthio)quinazolin-4(3H)-one (128.7 mg, 0.518 mmol, 30% yield) as a white solid: m/z (ESI, +ve) 249.2 (M+H)+. 8-(1-ethoxyvinyl)-3-methyl-2-(methylthio)quinazolin-4(3H)-one (35.5 mg, 0.128 mmol, 7% yield) as a colorless oil: m/z (ESI, +ve) 277.1 (M+H)+.

Workup

concentrationconcentrated onto silica gel
customChromatographic purification (silica gel, 0-50% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-6629f46d19ea47f3b3d3e9af0114d706
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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