Methyl Acrylate → methyl (2E)-3-(pyrimidin-5-yl)prop-2-enoate

HRID 474542ノート

反応式

HRID 474542 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[C:8]([O:12][CH3:13])(=[O:11])[CH:9]=[CH2:10]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[N:4]1[CH:3]=[C:2](/[CH:10]=[CH:9]/[C:8]([O:12][CH3:13])=[O:11])[CH:7]=[N:6][CH:5]=1

参加物

6

反応物 2

HCID 7294Methyl AcrylateHCID 783445-Bromopyrimidine

生成物 1

HCID 18470237methyl (2E)-3-(pyrimidin-5-yl)prop-2-enoate収率 66.4%

試薬・触媒・溶媒 3

HCID 80271Tri-o-tolylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 5-bromopyrimidine (22.82 g, 144 mmol), methyl 2-propenoate (14.83 g, 172 mmol), palladium(II) acetate (0.322 g, 1.435 mmol), tri-o-tolylphosphine (0.874 g, 2.87 mmol), and TEA (32.0 g, 316 mmol) in DMF (100 mL) was heated at 130° C. under N2 for 7 h. After cooling, the reaction mixture was partitioned between water (200 mL) and DCM (200 mL). The organic phase was collected, washed with water (200 mL×4), brine, dried over sodium sulphate, and concentrated in vacuo to give the crude title compound as a pale yellow solid (18.4 g, 95 mmol, 66.4%). LCMS: rt=1.01 min, [M+H+]=165

後処理

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water (200 mL) and DCM (200 mL)
  3. customThe organic phase was collected
  4. washwashed with water (200 mL×4), brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f5f7dcef2127411a9c0a9d80b76d682d
出典データセット
uspto-grants-2014_01
特許番号
US08637536B2

反応ノート

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