Tributyltin Chloride → (4-Benzyloxy-phenyl)-(6-(4-(1,3-dioxolan-2-yl)-3-methyl-3H-imidazol-2-yl)-quinazolin-4-yl)-amine

HRID 2306755Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)=[CH:5][N:4]=[CH:3]1.C([Li])CCC.C([Sn](Cl)(CCCC)CCCC)CCC.[CH2:31]([O:38][C:39]1[CH:44]=[CH:43][C:42]([NH:45][C:46]2[C:55]3[C:50](=[CH:51][CH:52]=[C:53](I)[CH:54]=3)[N:49]=[CH:48][N:47]=2)=[CH:41][CH:40]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Ag-]=O>[CH2:31]([O:38][C:39]1[CH:40]=[CH:41][C:42]([NH:45][C:46]2[C:55]3[C:50](=[CH:51][CH:52]=[C:53]([C:3]4[N:2]([CH3:1])[C:6]([CH:7]5[O:11][CH2:10][CH2:9][O:8]5)=[CH:5][N:4]=4)[CH:54]=3)[N:49]=[CH:48][N:47]=2)=[CH:43][CH:44]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 20 °C

Procedure

1-Methyl-5-(1,3-dioxolan-2-yl)-imidazole (0.09 g) in dry THF (5 ml) under N2 was cooled to −78° C. and treated with n-butyl lithium (0.4 ml, 1.6 M). After 30 minutes, tributyl tin chloride (0.17 ml) was added, the mixture allowed to warm to 20° C. and stirred for 1 hour. (4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amine (0.191 g), catalytic quantities of 1.4-bis-(diphenylphosphino)-butane palladium (II) chloride and silver (I) oxide (0.052 g) were added and the mixture heated at reflux for 18 hours. The mixture was absorbed onto silica and chromatographed to give the title compound (0.045 g); m/z (M+1)+ 480.

Workup

temperaturethe mixture heated
temperatureat reflux for 18 hours
customThe mixture was absorbed onto silica
customchromatographed

Sources & evidence

ORD record: ord-03c194545f66477fa05a900d76dd0e1b
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828320B2

Reaction notes

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