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Triethylamine → HCID 59834732, 화합물

HRID 271594
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인쇄 미리보기

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HRID 271594 반응식
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=1)[C:2]#[CH:3].Br[C:13]1[C:14]([NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[N:15][C:16]([C:19]#[N:20])=[N:17][CH:18]=1.C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH:22]1([N:21]2[C:14]3[N:15]=[C:16]([C:19]#[N:20])[N:17]=[CH:18][C:13]=3[CH:3]=[C:2]2[CH2:1][C:4]2[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 11332545(4-prop-2-ynyl-phenyl)-methanolHCID 17968181HCID 17968181, 화합물

생성물 1

HCID 59834732HCID 59834732, 화합물수율 107.2%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

To a solution of (4-prop-2-ynyl-phenyl)-methanol (10 mmol) and 5-bromo-4-cyclohexylamino-pyrimidine-2-carbonitrile (7 mmol) in DMF (20 ml) are added triethylamine (21 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.35 mmol) and copper (I) iodide (0.7 mmol). The reaction mixture is heated at 85° C. ca. for 2 h. The reaction mixture is quenched with saturated ammonium chloride and extracted with AcOEt. The organic layer is washed with brine and then dried over sodium sulfate and concentrated under vacuum to give 2.6 g of crude product, which is purified by silica gel column chromatography. Yield 58%.

후처리

  1. customThe reaction mixture is quenched with saturated ammonium chloride
  2. extractionextracted with AcOEt
  3. washThe organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-94beb143ef7b4653b204476fb4c1cd53
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07452886B2

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