Diisopropylamine → 2-(Methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine

HRID 1159873노트

반응식

HRID 1159873 반응식
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C(NC(C)C)(C)C.[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=1)#[CH:18]>C1COCC1.[Cu]I.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>[CH3:9][S:8][C:4]1[N:3]=[C:2]([C:18]#[C:17][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[CH:7]=[CH:6][N:5]=1

참가 물질

7

반응물 3

HCID 7912DiisopropylamineHCID 76432Benzene, 1-ethynyl-3-nitro-HCID 38589014-Iodo-2-(methylthio)pyrimidine

생성물 1

HCID 595114132-(Methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine수율 98.6%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
25 °C

실험 절차

4-Iodo-2-(methylthio)pyrimidine (39.7 g, 0.157 mol) and diisopropylamine (44.2 mL, 0.315 mol) are dissolved in dry THF (720 mL) and argon gas is bubbled through the solution for 20 min. Copper(I) iodide (2.99 g, 14.3 mmol) and bis(triphenylphosphine)palladium dichloride (5.51 g, 7.85 mmol) are added and then 1-ethynyl-3-nitrobenzene (25.4 g, 0.173 mol) in dry THF (100 mL) is added dropwise over about 30 min with the temperature being maintained at about 25° C. Following complete addition, the mixture is stirred at rt for overnight. The mixture is filtered and washed with THF. The filtrate is concentrated under reduced pressure. The residue is washed with EtOAc/MeOH to give pale-yellow solid (42 g).

후처리

  1. customargon gas is bubbled through the solution for 20 min
  2. additionaddition
  3. filtrationThe mixture is filtered
  4. washwashed with THF
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. washThe residue is washed with EtOAc/MeOH

출처 및 근거

ORD 기록
ord-bf6200784b3c445ba41e7483d3b50551
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812022B2

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