Ammonium Chloride → (S)-3-(4-Bromophenyl)-1-(2-methoxypyrimidin-5-yl)-3-o-tolylpropan-1-one

HRID 1618052ノート

反応式

HRID 1618052 の反応式
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][C:10]([O:13][CH3:14])=[N:11][CH:12]=1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:23][C:24](N(OC)C)=[O:25])=[CH:18][CH:17]=1.[Cl-].[NH4+]>O1CCCC1>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([C@@H:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:23][C:24]([C:7]2[CH:8]=[N:9][C:10]([O:13][CH3:14])=[N:11][CH:12]=2)=[O:25])=[CH:20][CH:21]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 139657Pyrimidine, 5-bromo-2-methoxy-HCID 71813343(S)-3-(4-bromophenyl)-N-methoxy-N-methyl-3-o-tolylpropanamideHCID 178418339Butyllithium

生成物 1

HCID 67015720(S)-3-(4-Bromophenyl)-1-(2-methoxypyrimidin-5-yl)-3-o-tolylpropan-1-one収率 38.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of n-butyllithium (1.6 M in hexane, 3.31 mL, 5.3 mmol) in tetrahydrofuran (12 mL) was cooled to −95° C. and added dropwise, under nitrogen, to a stirred, cooled (−95° C.) solution of 5-bromo-2-methoxypyrimidine (1.00 g, 5.3 mmol) in dry tetrahydrofuran (40 mL). To the resulting yellow solution was immediately added a solution of (S)-3-(4-bromophenyl)-N-methoxy-N-methyl-3-o-tolylpropanamide (example 142, step 1; 1.6 g, 4.42 mmol) in dry THF (12 mL), with the temperature of the reaction mixture being kept between −90° C. and −100° C. The solution was stirred and allowed to warm to room temperature over 2 h. The reaction mixture was poured onto sat. aq. ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound (700 mg, 35%), Colourless gum, MS (ESI+): m/z=: 411.2 [M+H]+.

後処理

  1. additionadded dropwise, under nitrogen, to a stirred
  2. custombeing kept between −90° C. and −100° C
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-be7143772928470d96bb2143f067337c
出典データセット
uspto-grants-2014_07
特許番号
US08765730B2

反応ノート

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