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Triethylamine → Methyl 2-{4-[(7-amino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)ethynyl]phenyl}-2-methylpropanoate

HRID 657699
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HRID 657699 반응식
[C:1]([C:3]1[C:4]([CH3:13])=[N:5][C:6]2[N:7]([N:10]=[CH:11][N:12]=2)[C:8]=1[NH2:9])#[CH:2].Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1.C(N(CC)CC)C>C(#N)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>[NH2:9][C:8]1[N:7]2[N:10]=[CH:11][N:12]=[C:6]2[N:5]=[C:4]([CH3:13])[C:3]=1[C:1]#[C:2][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1
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7

반응물 3

HCID 8471TriethylamineHCID 3651431Methyl 2-(4-bromophenyl)-2-methylpropanoateHCID 871324066-Ethynyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

생성물 1

HCID 25105932Methyl 2-{4-[(7-amino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)ethynyl]phenyl}-2-methylpropanoate수율 45.8%

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 6342Acetonitrile용매

실험 절차

A mixture of Example 72B (17 mg, 0.1 mmol), methyl 2-(4-bromophenyl)-2-methylpropanoate (38 mg, 0.15 mmol), bis(triphenylphosphine)palladium(II) dichloride (3.5 mg, 0.005 mmol), CuI (1 mg, 0.005 mmol), and triethylamine (28 μL, 0.2 mmol) in acetonitrile (500 μL) was heated at 95° C. under nitrogen for 1 h. The resulting mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuuo. The residue was purified by flash chromatograph on silica gel (eluting with ethyl acetate) to provide the title compound as a white solid (16 mg, 45% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.44 (s, 3H), 7.64 (d, J=8.48 Hz, 2H), 7.36 (d, J=8.48 Hz, 2H), 3.61 (s, 3H), 2.60 (s, 3H), 1.52 (s, 6H). MS (ESI) m/z 350 (M+H)+.

후처리

  1. customThe resulting mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuuo
  6. customThe residue was purified by flash chromatograph on silica gel (eluting with ethyl acetate)

출처 및 근거

ORD 기록
ord-975eaa8ea37a4dc7a1404bf8b38f6712
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08076344B2

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