Tributylvinyltin → HCID 18670535, compound

HRID 1059444Notes

Reaction equation

HRID 1059444 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.[CH:29]([Sn](CCCC)(CCCC)CCCC)=[CH2:30]>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>[CH3:27][O:26][CH2:25][N:17]1[C:16]2[CH:28]=[C:12]([CH2:11][N:4]3[C:3]4[C:7](=[N:8][CH:9]=[N:10][C:2]=4[CH:29]=[CH2:30])[N:6]=[CH:5]3)[CH:13]=[CH:14][C:15]=2[S:20][C:19]2[N:21]=[CH:22][CH:23]=[N:24][C:18]1=2

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 18670590HCID 18670590, compound

Product 1

HCID 18670535HCID 18670535, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.30 g of 8-(6-chloropurin-7-ylmethyl)-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine in N,N-dimethylformamide (10 ml) were added in a nitrogen atmosphere 0.312 g of vinyl-tri-n-butyltin (IV) and 0.050 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 0.19 g of 10-methoxymethyl-8-(6-vinylpurin-7-ylmethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine as a yellow solid. To a solution of 190 mg of the obtained compound in methanol (20 ml) was added 0.018 g of palladium/carbon and hydrogenation was effected in a hydrogengas stream for 2 hours. Thus, 0.10 g of the title compound was obtained as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-af8ee75c7d05439f80e89273de2d8077
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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