Hexamethylditin → (2,3-Dihydro-2,2-dimethyl-3-benzofuranon-4-yl)tin

HRID 726589Notes

Reaction equation

HRID 726589 reaction equation
Br[C:2]1[C:7]2[C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C[Sn:15](C)C.C[Sn](C)C>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:11][C:9]1([CH3:12])[C:8](=[O:13])[C:7]2[C:2]([Sn:15])=[CH:3][CH:4]=[CH:5][C:6]=2[O:10]1

Participants

5

Reactant 2

HCID 6327618HexamethylditinHCID 543779064-Bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone

Product 1

HCID 131719446(2,3-Dihydro-2,2-dimethyl-3-benzofuranon-4-yl)tin

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

In a slight variation in the method to the 2,4-diamino-5,6-disubstituted-5-deazapteridine described above, using a method taught by A. Pidcock et al (J. Organometallic Chem. 1981, 215, 49-58), 4-bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone is reacted with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(O) in toluene, yielding (2,3-dihydro-2,2-dimethyl-3-benzofuranon-4-yl)tin. The organometallic derivative is then reacted with 2-amino-3-cyano-5-iodo-4-methylpyridine, again in the presence of tetrakis(triphenylphosphine)palladium(O) in toluene, affording the corresponding 2-amino-3-cyano-5-(2,3-dihydro-2,2-dimethyl-3-benzofuranon-4-yl)-4-methylpyridine. This compound is then cyclized with guanidine in ethanol, as previously described, yielding the corresponding 2,4-diamino-5-methyl-6-(2,3-dihydro-2,2-dimethyl-3-benzofuranon-4-yl)-5-deazapteridine. Example 9 provides a detailed description of how this reaction is conducted.

Sources & evidence

ORD record
ord-2eb08687e6194d2abaeb0ce714683d86
Source dataset
uspto-grants-1998_01
Patent number
US05710157

Reaction notes

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