Pyridazine → 4-(Tributylstannyl)pyrimidine

HRID 1359285노트

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HRID 1359285 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 178300604-(Tributylstannyl)pyrimidine

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b20b76820cb44d158fe2ed2d4de81a7f
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599917B1

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