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

HRID 349224노트

반응식

HRID 349224 반응식
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

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

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%).

후처리

  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%))

출처 및 근거

ORD 기록
ord-8c86f036660d403a8cf61ccb24dff528
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179812B2

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