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

HRID 2306755노트

반응식

HRID 2306755 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)촉매HCID 178418778HCID 178418778, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
20 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-03c194545f66477fa05a900d76dd0e1b
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828320B2

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