Pyrimidine → 4-(Tributylstannyl)pyrimidine

HRID 1359283ノート

反応式

HRID 1359283 の反応式
C([Li])CCC.CC1(C)CCCC(C)(C)N1.[N:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=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:16]1[CH:21]=[CH:20][C:19]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])=[N:18][CH:17]=1

参加物

8

反応物 4

HCID 9260PyrimidineHCID 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

5.8 ml of a hexane solution containing 2.52 mol of n-butyllithium was slowly added dropwise into a solution of 20 ml of tetrahydrofuran containing 2.5 ml of 2,2,6,6-tetramethylpiperidine. After stirring at 0° C. for 30 minutes, a mixture of 0.98 ml of pyrimidine, 4.6 ml of tri-n-butyltin chloride and 20 ml of tetrahydrofuran was slowly added dropwise thereinto. 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 silica gel column chromatography to elute with hexane/ethyl acetate (10:1), to give 474 mg of the target compound.

後処理

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

出典と根拠

ORDレコード
ord-8546d8822e6c42818a7233f527c31070
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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