Diisopropylamine → 5-(4-[1,2,3]Triazol-1-yl-but-1-ynyl)-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

HRID 349224ノート

反応式

HRID 349224 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[N:11]=[C:12]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[O:13][CH:14]=2)=[N:6][CH:7]=1.[CH2:27]([N:31]1[CH:35]=[CH:34][N:33]=[N:32]1)[CH2:28][C:29]#[CH:30].C(NC(C)C)(C)C.C(OCC)(=O)C>CN(C=O)C.C1COCC1.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:31]1([CH2:27][CH2:28][C:29]#[C:30][C:2]2[CH:3]=[N:4][C:5]([O:8][CH2:9][C:10]3[N:11]=[C:12]([CH:15]=[CH:16][C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=4)[O:13][CH:14]=3)=[N:6][CH:7]=2)[CH:35]=[CH:34][N:33]=[N:32]1

参加物

9

反応物 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 184535221-But-3-ynyl-1H-[1,2,3]triazoleHCID 694890165-Bromo-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

生成物 1

HCID 694883845-(4-[1,2,3]Triazol-1-yl-but-1-ynyl)-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of 5-bromo-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine (0.213 g, 0.50 mmol), 1-but-3-ynyl-1H-[1,2,3]triazole (0.067 g, 0.55 mmol) and diisopropyl amine (iPr2NH) (2 ml) in DMF (4 ml) and THF (2 ml), copper iodide (CuI) (0.0048 g, 0.025 mmol) is added under stirring. After passing a stream of argon through the mixture for 10 min tetrakis(triphenylphosphine)palladium (0.029 g, 0.025 mmol) is added and the mixture is heated at 80° C. for 3 h. Ethyl acetate (150 ml) is added, the resulting mixture is washed with ammonium chloride (NH4Cl) and brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (chloroform (100%)->ethyl acetate (100%)) yielding 5-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine as a pale yellow solid. Yield 138 mg (59%).

後処理

  1. customfor 10 min
  2. additionis added
  3. washthe resulting mixture is washed with ammonium chloride (NH4Cl) and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash column chromatography (chloroform (100%)->ethyl acetate (100%))

出典と根拠

ORDレコード
ord-8c86f036660d403a8cf61ccb24dff528
出典データセット
uspto-grants-2007_02
特許番号
US07179812B2

反応ノート

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