4-Amino-5-bromo-2-chloropyrimidine → 2-Chloro-5-(2-ethoxyvinyl)pyrimidin-4-amine

HRID 1619125ノート

反応式

HRID 1619125 の反応式
Br[C:2]1[C:3]([NH2:9])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)/[CH:15]=[CH:16]\[O:17][CH2:18][CH3:19])CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:5]1[N:4]=[C:3]([NH2:9])[C:2](/[CH:15]=[CH:16]/[O:17][CH2:18][CH3:19])=[CH:7][N:6]=1

参加物

5

反応物 2

HCID 27632934-Amino-5-bromo-2-chloropyrimidineHCID 5706773cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene2 回

生成物 1

HCID 112871092-Chloro-5-(2-ethoxyvinyl)pyrimidin-4-amine収率 32%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

To a degassed suspension of 5-bromo-2-chloropyrimidin-4-amine (preparation 37a, 2.50 g, 11.03 mmol) and (Z)-tributyl(2-ethoxyvinyl)stannane (4.76 g, 11.20 mmol) in toluene (40 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.42 g, 0.36 mmol) and the mixture was subjected to several vacuum-argon cycles and then heated to reflux for 24 hours. Further catalyst (0.42 g, 0.36 mmol) was added and the mixture was refluxed an additional 24 hours. Further (Z)-tributyl(2-ethoxyvinyl)stannane (1.20 g, 2.82 mmol) was added and the reaction was refluxed overnight. The mixture was cooled and concentrated in vacuo and the oily residue was treated with hexanes to give a solid which was purified by flash chromatography (4:1 hexanes/ethyl acetate) to give the title compound (0.70 g, 32%) as a white solid.

後処理

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. temperaturethe mixture was refluxed an additional 24 hours
  4. temperaturethe reaction was refluxed overnight
  5. temperatureThe mixture was cooled
  6. concentrationconcentrated in vacuo
  7. additionthe oily residue was treated with hexanes
  8. customto give a solid which
  9. customwas purified by flash chromatography (4:1 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-6fe11f3a56b3461eb7c32d9f2b27ffd1
出典データセット
uspto-grants-2014_07
特許番号
US08772288B2

反応ノート

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