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

HRID 1157538노트

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HRID 1157538 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

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온도
25 °C

실험 절차

4-Iodo-2-(methylthio)pyrimidine (39.7 g, 0.157 mol) and diisopropylamine (44.2 mL, 0.315 mol) were dissolved in dry THF (720 mL) and argon gas was 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) were added and then 1-ethynyl-3-nitrobenzene (25.4 g, 0.173 mol) in dry THF (100 mL) was added dropwise over about 30 min with the temperature being maintained at about 25° C. Following complete addition, the mixture was stirred at rt overnight. The mixture is filtered and washed with THF. The filtrate is concentrated under reduced pressure. The residue was washed with EtOAc/MeOH to give pale-yellow solid (42 g).

후처리

  1. customargon gas was 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 was washed with EtOAc/MeOH

출처 및 근거

ORD 기록
ord-3fbab6cfe1fe4c10a2daa7d40cf6a5bd
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807673B2

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