tert-Butyl methyl ether → Methyl 2-chloro-6-(1-ethoxyvinyl)pyrimidine-4-carboxylate

HRID 59113

反応式

HRID 59113 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.C([Sn](CCCC)(CCCC)[C:18]([O:20][CH2:21][CH3:22])=[CH2:19])CCC.[F-].[K+].CC(OC)(C)C>CN(C=O)C.O.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>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([C:18]([O:20][CH2:21][CH3:22])=[CH2:19])[N:3]=1

参加物

8

反応物 4

HCID 15413tert-Butyl methyl etherHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

生成物 1

HCID 117821404Methyl 2-chloro-6-(1-ethoxyvinyl)pyrimidine-4-carboxylate収率 75%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
94 °C

実験手順

Methyl 2,6-dichloropyrimidine-4-carboxylate (8.44 g, 40.77 mmol) and bis(triphenylphosphine)-palladium(II) chloride (0.572 g, 0.82 mmol) in DMF (80 mL) was degased. Tributyl(1-ethoxy-vinyl)tin (14.46 mL, 42.81 mmol) was added under argon. The mixture was heated at 94° C. for 1 h. The mixture was poured into a solution of potassium fluoride (30 g) in water (400 mL). MTBE (300 mL) was added and the mixture was stirred for 10 min. The mixture was filtered and the filter was washed with 200 mL of MTBE. The filtrate was washed with brine (100 mL), dried over sodium sulfate and the solvents were evaporated. The residue purified by column chromatography on silica eluting with DCM to give the title compound as a solid (7.40 g, 75%).

後処理

  1. filtrationThe mixture was filtered
  2. washthe filter was washed with 200 mL of MTBE
  3. washThe filtrate was washed with brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. customthe solvents were evaporated
  6. customThe residue purified by column chromatography on silica eluting with DCM

出典と根拠

ORDレコード
ord-04fc7098ba644efc9570b0c89b16e660
出典データセット
uspto-grants-2016_09
特許番号
US09439904B2

関連ノート

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