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Benzyl Bromide → Methyl 2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)-3-phenylpropanoate

HRID 1399694
ノート
印刷プレビュー

反応式

HRID 1399694 の反応式
[CH3:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:5]=[C:4]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[N:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.[CH2:41](Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C>[CH3:1][C:2]1[C:7]([CH:8]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:5]=[C:4]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[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

6

反応物 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 2733832Lithium hexamethyldisilazaneHCID 66955539Methyl 2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)acetate

生成物 1

HCID 50995547Methyl 2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)-3-phenylpropanoate収率 68.7%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
-15 °C

実験手順

To a cooled (−15° C.) solution of methyl 2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)acetate (0.100 g; 0.295 mmol) in dry DMF (1.5 mL) was wadded a 1N solution of LHMDS in THF (0.324 mL; 0.324 mmol) dropwise and the mixture was stirred at (−15° C.) for 15 min, followed by the dropwise addition of benzyl bromide (0.070 mL; 0.589 mmol). After stirring for 2 h at (−15° C.) the mixture was allowed to warm up to room temperature. After 1 h the reaction was quenched by adding a saturated solution of ammonium chloride and the mixture was extracted twice with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane furnished 0.087 g (60%) of the title compound as a colorless oil.

後処理

  1. stirringAfter stirring for 2 h at (−15° C.) the mixture
  2. temperatureto warm up to room temperature
  3. customAfter 1 h the reaction was quenched
  4. additionby adding a saturated solution of ammonium chloride
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane

出典と根拠

ORDレコード
ord-376e74be1ff043c1a9b9f7901dea3caa
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08906906B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート