Potassium Carbonate → E-5-(2-Bromovinyl)-2,4-dimethoxypyrimidine

HRID 440718ノート

反応式

HRID 440718 の反応式
C(/[CH:4]=[CH:5]/[C:6]1[C:7]([O:14][CH3:15])=[N:8][C:9]([O:12][CH3:13])=[N:10][CH:11]=1)(O)=O.C([O-])([O-])=O.[K+].[K+].[Br:22]N1C(=O)CCC1=O>CN(C=O)C>[Br:22]/[CH:4]=[CH:5]/[C:6]1[C:7]([O:14][CH3:15])=[N:8][C:9]([O:12][CH3:13])=[N:10][CH:11]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 688432(E)-5-(2-Carboxyvinyl)-2,4-dimethoxypyrimidine

生成物 1

HCID 15928608E-5-(2-Bromovinyl)-2,4-dimethoxypyrimidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of E-5-(2-carboxyvinyl)-2,4-dimethoxypyrimidine (0.300 g; 1.43 retool) in dry DMF (5 ml) was added K2CO3 (0.45 g: 5.25 mmol). After stirring at ambient temperature for 15 min. a solution of N-bromosuccinimide (0.258 g; 1.45 mmol) in dry DMF (4 ml) was added dropwise over 10 min. The suspension was immediately filtered, the solid washed with DMF and the filtrate evaporated in high vacuum. The solid residue was purified by column chromatography by preloading on SiO2 and eluting with EtOAc-hexane (7:3, v/v). Product fractions were pooled and evaporated to give fine white crystals, yield 0.561 g (45%). FAB mass spectrum: m/z245 and 247 (M+H)+. Analysis, found: C,39.9; H, 3.6; N, 11.5% C8H9BrN2O2 requires C, 40.20; H, 3.70; N. 11.43%.

後処理

  1. additionwas added dropwise over 10 min
  2. filtrationThe suspension was immediately filtered
  3. washthe solid washed with DMF
  4. customthe filtrate evaporated in high vacuum
  5. customThe solid residue was purified by column chromatography
  6. washeluting with EtOAc-hexane (7:3
  7. customevaporated
  8. customto give fine white crystals, yield 0.561 g (45%)

出典と根拠

ORDレコード
ord-40eb5c33b73049cfb0ea5c5ad8a8ee30
出典データセット
uspto-grants-1996_05
特許番号
US05521163

反応ノート

読み込み中…