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

HRID 2306755ノート

反応式

HRID 2306755 の反応式
[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

参加物

8

反応物 4

HCID 15096Tributyltin ChlorideHCID 21951950(4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amineHCID 226098451-Methyl-5-(1,3-dioxolan-2-yl)-imidazoleHCID 178418339Butyllithium

生成物 1

HCID 22609737(4-Benzyloxy-phenyl)-(6-(4-(1,3-dioxolan-2-yl)-3-methyl-3H-imidazol-2-yl)-quinazolin-4-yl)-amine収率 22.3%

試薬・触媒・溶媒 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)触媒HCID 178418778HCID 178418778、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hours
  3. customThe mixture was absorbed onto silica
  4. customchromatographed

出典と根拠

ORDレコード
ord-03c194545f66477fa05a900d76dd0e1b
出典データセット
uspto-grants-2004_12
特許番号
US06828320B2

反応ノート

読み込み中…