N-bromobutanimide → 2-Bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanone

HRID 633733ノート

反応式

HRID 633733 の反応式
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[CH:10][C:9]([C:12]([O:14]CC)=[CH2:13])=[CH:8][N:7]=2)[CH2:3][CH2:2]1.[Br:17]N1C(=O)CCC1=O>C1COCC1.O.C(OCC)(=O)C>[Br:17][CH2:14][C:12]([C:9]1[CH:8]=[N:7][C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[N:11][CH:10]=1)=[O:13]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 1181998532-Cyclopropylmethoxy-5-(1-ethoxyvinyl)pyrimidine

生成物 1

HCID 1181998522-Bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanone収率 71.7%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

A solution of 480 mg (2.18 mmol) of 2-cyclopropylmethoxy-5-(1-ethoxyvinyl)pyrimidine in 8 mL of a THF/H2O mixture: (6/2: v/v) is cooled to 0° C. under argon. After addition of 380.02 mg (2.11 mmol) of N-bromosuccinimide, the reaction mixture is maintained at 0° C. for 1 hour. The solution obtained is taken up in ethyl acetate and washed with aqueous NaHCO3 solution and then with saturated NaCl solution. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 80/20 DCM/MeOH) to give 410 mg of 2-bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanone, the characteristics of which are as follows:

後処理

  1. customThe solution obtained
  2. washwashed with aqueous NaHCO3 solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography on silica gel (eluent: 80/20 DCM/MeOH)

出典と根拠

ORDレコード
ord-9372a79e407c4764adbbc7f5b1a76598
出典データセット
uspto-grants-2016_04
特許番号
US09321790B2

反応ノート

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