Stannane, tributyl(1-ethoxyethenyl)- → HCID 18670529, compound

HRID 1059445Notes

Reaction equation

Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]3[S:20][C:19]4[N:21]=[CH:22][CH:23]=[N:24][C:18]=4[N:17]([CH2:25][O:26][CH3:27])[C:16]=3[CH:28]=1)[CH:5]=[N:6]2.[CH2:29]([O:31][C:32]([Sn](CCCC)(CCCC)CCCC)=[CH2:33])[CH3:30]>CN(C)C=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:32]([O:31][C:29]([C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]3[S:20][C:19]4[N:21]=[CH:22][CH:23]=[N:24][C:18]=4[N:17]([CH2:25][O:26][CH3:27])[C:16]=3[CH:28]=1)[CH:5]=[N:6]2)=[CH2:30])[CH3:33]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 0.9 g of 8-(6-chloropurin-7-ylmethyl)-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine in N,N-dimethylformamide (15 ml) were added in a nitrogen atmosphere 1.03 g of 1-ethoxyvinyl-tri-n-butyltin (IV) and 0.015 g of bis(triphenylphosphine) palladium (II) chloride. After degassing, the mixture was heated to 80° C. for 20 hours. Then the insoluble matters were removed by filtering through celite. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.77 g of the title compound as yellow crystals.

Workup

customAfter degassing
customThen the insoluble matters were removed
filtrationby filtering through celite
distillationAfter distilling off the solvent under reduced pressure
customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record: ord-0d7cc7edd80d443a9c84f0875237636d
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518423B1

Reaction notes

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