Pyridazine → 4-(Tributylstannyl)pyrimidine

HRID 1359285ノート

反応式

HRID 1359285 の反応式
C([Li])CCC.C[C:7]1(C)[CH2:12][CH2:11]C[C:9](C)(C)[NH:8]1.[N:16]1C=CC=CN=1.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>O.O1CCCC1.CCCCCC>[N:8]1[CH:7]=[CH:12][C:11]([Sn:26]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:22][CH2:23][CH2:24][CH3:25])=[N:16][CH:9]=1

参加物

8

反応物 4

HCID 9259PyridazineHCID 130352,2,6,6-TetramethylpiperidineHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

生成物 1

HCID 178300604-(Tributylstannyl)pyrimidine

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

58.0 ml of a hexane solution containing 2.52 mol of n-butyllithium was slowly added dropwise into a solution of 200 ml of tetrahydrofuran containing 25.0 mol of 2,2,6,6-tetramethylpiperidine at −30° C. After stirring at 0° C. for 30 minutes, a mixture of 9.1 ml of pyridazine, 46.0 ml of tri-n-butyltin chloride and 100 ml of tetrahydrofuran was slowly added dropwise thereinto at −78° C. After stirring at −78° C. for 4 hours, water was added to the reaction solution and then extracted with ethyl acetate. The organic phase was washed with brine and the solvent was removed. Then, the residue was subjected to NH-silica gel (Fuji Silicia) column chromatography and eluted with hexane/ethyl acetate (10:1). Then, it was subjected to silica gel chromatography and eluted with hexane/ethyl acetate (10:1) and then with hexane/ethyl acetate (1:1), to give 6.6 g of the target compound.

後処理

  1. additionwas slowly added dropwise
  2. customat −78° C
  3. stirringAfter stirring at −78° C. for 4 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. customthe solvent was removed
  7. washeluted with hexane/ethyl acetate (10:1)
  8. washeluted with hexane/ethyl acetate (10:1)

出典と根拠

ORDレコード
ord-b20b76820cb44d158fe2ed2d4de81a7f
出典データセット
uspto-grants-2003_07
特許番号
US06599917B1

反応ノート

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