5-Bromo-2-chloropyrimidine → 2-chloro-5-[(Z)-2-ethoxyethenyl]pyrimidine

HRID 716740ノート

反応式

HRID 716740 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)/[CH:14]=[CH:15]\[O:16][CH2:17][CH3:18])CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:8][C:5]1[N:4]=[CH:3][C:2](/[CH:14]=[CH:15]\[O:16][CH2:17][CH3:18])=[CH:7][N:6]=1

参加物

5

反応物 2

HCID 6066655-Bromo-2-chloropyrimidineHCID 5706773cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene

生成物 1

HCID 866913322-chloro-5-[(Z)-2-ethoxyethenyl]pyrimidine収率 32.7%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A mixture of 5-bromo-2-chloropyrimidine (800 mg), CIS-tributyl[2-ethoxyethenyl] tin (1.80 g), PdCl2(PPh3)2 (30 mg), and toluene (10 mL) was stirred under a nitrogen atmosphere at an outside temperature of 100° C. for 4 hours. After cooling, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (SNAP Cartridge KP-NH: 28 g, mobile phase: n-hexane/EtOAc=100/0 to 85/15 (v/v)) to yield 2-chloro-5-[(Z)-2-ethoxyethenyl]pyrimidine (250 mg, colorless solid).

後処理

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by column chromatography (SNAP Cartridge KP-NH: 28 g, mobile phase: n-hexane/EtOAc=100/0 to 85/15 (v/v))

出典と根拠

ORDレコード
ord-4284070172bf4e90afc238e19ce7eb39
出典データセット
uspto-grants-2015_11
特許番号
US09193695B2

反応ノート

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