Triethylamine → Ethyl 3-(pyrimidin-5-yl)prop-2-enoate

HRID 2228907ノート

反応式

HRID 2228907 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[C:8]([O:12][CH2:13][CH3:14])(=[O:11])[CH:9]=[CH2:10].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[N:4]1[CH:3]=[C:2]([CH:10]=[CH:9][C:8]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[N:6][CH:5]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 783445-Bromopyrimidine

生成物 1

HCID 53438539Ethyl 3-(pyrimidin-5-yl)prop-2-enoate収率 71.9%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

A mixture of 5-bromopyrimidine (5.93 g), ethyl acrylate (5.08 g), palladium acetate (0.112 g), triphenyl phosphine (0.23 g) and triethylamine (4.5 g) was stirred at 150° C. in a pressure vessel for 6 hours. After cooling overnight, water (50 ml) was added to the dark residue, and the product was extracted into toluene. Drying, charcoaling and evaporation gave a pale oil, which was triturated with pet, ether to obtain ethyl 3-(5-pyrimidyl)acrylate (4.78 g). 1H-NMR (CDCl3) δ 1.36 (3H, t), 4.27 (2H, q), 6.59 (1H, d), 7.62 (1H, d), 8.88 (2H, s), 9.20 (1H, s).

後処理

  1. temperatureAfter cooling overnight
  2. extractionthe product was extracted into toluene
  3. customDrying
  4. customcharcoaling and evaporation
  5. customgave a pale oil, which
  6. customwas triturated with pet, ether

出典と根拠

ORDレコード
ord-8b5f2d5d11c149ac90d9567b38c7e7b8
出典データセット
uspto-grants-2002_07
特許番号
US06417192B1

反応ノート

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