Tetrabutylammonium Fluoride → 3-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-2-methyl-5-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one

HRID 1718524ノート

反応式

HRID 1718524 の反応式
[CH3:1][C:2]1([CH3:53])[CH2:11][CH:10]([O:12][Si](C(C)C)(C(C)C)C(C)C)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:23]3[C:28](=[O:29])[C:27]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=5[C:43]5[NH:47][C:46](=[O:48])[O:45][N:44]=5)=[CH:33][CH:32]=4)=[C:26]([CH2:49][CH2:50][CH3:51])[N:25]=[C:24]3[CH3:52])[CH:8]=2)[O:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:12][CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:23]3[C:28](=[O:29])[C:27]([CH2:30][C:31]4[CH:32]=[CH:33][C:34]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=5[C:43]5[NH:47][C:46](=[O:48])[O:45][N:44]=5)=[CH:35][CH:36]=4)=[C:26]([CH2:49][CH2:50][CH3:51])[N:25]=[C:24]3[CH3:52])[CH:8]=2)[O:3][C:2]([CH3:1])([CH3:53])[CH2:11]1

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 1361467753-{2,2-dimethyl-4-[(triisopropylsilyl)oxy]-3,4-dihydro-2H-chromen-6-yl}-2-methyl-5-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one

生成物 1

HCID 1359558823-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-2-methyl-5-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one収率 95.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-{2,2-dimethyl-4-[(triisopropylsilyl)oxy]-3,4-dihydro-2H-chromen-6-yl}-2-methyl-5-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one (4.0 g) in tetrahydrofuran (20 mL) was added tetrabutylammonium fluoride (1.0 M tetrahydrofuran solution, 8.2 mL), and the mixture was stirred for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogen sulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (3.0 g, 95%) as a solid.

後処理

  1. washwashed with 5% aqueous potassium hydrogen sulfate solution
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fc704b93bbf445c8b218bdb357daa186
出典データセット
uspto-grants-2010_09
特許番号
US07803940B2

反応ノート

読み込み中…