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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
ノート
印刷プレビュー

反応式

HRID 2093481 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c16d0230ac5542ef8e0b14d453917adb
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08445499B2

反応ノート

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