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N,N,N',N'-Tetramethylethylenediamine → 4-Methyl-6-(4-(1-(5-methylpyrazin-2-yl)piperidin-4-yl)piperidin-1-yl)pyrimidine-2-carbonitrile

HRID 2093481
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HRID 2093481 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]4[CH:25]=[N:24][C:23]([CH3:26])=[CH:22][N:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:27])[N:3]=1.C1(P(C2C=CC=CC=2)CCCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:59][N:60](C)CCN(C)C.[C-]#N.[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:27][C:4]1[CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]4[CH:25]=[N:24][C:23]([CH3:26])=[CH:22][N:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[N:7]=[C:2]([C:59]#[N:60])[N:3]=1
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참가 물질

7

반응물 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 9032Potassium CyanideHCID 27334141,5-Bis(diphenylphosphino)pentaneHCID 591789101-(2-Chloro-6-methylpyrimidin-4-yl)-1'-(5-methylpyrazin-2-yl)-4,4'-bipiperidine

생성물 1

HCID 545867804-Methyl-6-(4-(1-(5-methylpyrazin-2-yl)piperidin-4-yl)piperidin-1-yl)pyrimidine-2-carbonitrile

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

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온도
140 °C

실험 절차

The 1-(2-chloro-6-methylpyrimidin-4-yl)-1′-(5-methylpyrazin-2-yl)-4,4′-bipiperidine (700 mg, 1.8 mmol) was placed in a pressure tube and anhydrous toluene (4 mL) added. To the stirred solution was added: palladium(II) acetate (41 mg, 0.18 mmol), 1,5-bis(dipenylphosphino)pentane (159 mg, 0.36 mmol), N,N,N′,N′-tetramethylethylenediamine (0.11 mL, 0.724 mmol), and potassium cyanide (235 mg, 3.62 mmol). The vessel was degassed with N2, sealed and heated at 140° C. for 16 hours. The mixture was allowed to cool to r.t., diluted with ethyl acetate (50 mL), washed with brine (10 mL×1), dried over magnesium sulfate, filtered and concentrated in vac. The residue was purified by chromatography on silica gel with 20% acetone: hexanes to yield the title compound.

후처리

  1. additionTo the stirred solution was added
  2. customThe vessel was degassed with N2
  3. customsealed
  4. temperatureto cool to r.t.
  5. additiondiluted with ethyl acetate (50 mL)
  6. washwashed with brine (10 mL×1)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vac
  10. customThe residue was purified by chromatography on silica gel with 20% acetone

출처 및 근거

ORD 기록
ord-c16d0230ac5542ef8e0b14d453917adb
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08445499B2

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