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Bromine → 3-Bromo-7-methylimidazo[1,2-a]pyrimidine

HRID 478217
ノート
印刷プレビュー

反応式

HRID 478217 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[N:3]=1.C([O-])(=O)C.[Na+].[Br-:16].[K+].BrBr>CO>[Br:16][C:8]1[N:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[N:3][C:4]2=[N:10][CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24408BromineHCID 253877Potassium BromideHCID 517045Sodium AcetateHCID 113324927-Methylimidazo[1,2-a]pyrimidine

生成物 1

HCID 114015833-Bromo-7-methylimidazo[1,2-a]pyrimidine収率 63%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

7-Methylimidazo[1,2-a]pyrimidine (100 mg, 0.75 mmol) and sodium acetate (74 mg, 0.90 mmol) were dissolved in methanol (2 ml) which had been saturated with potassium bromide and this mixture was cooled to −10° C. before dropwise addition of bromine (132 mg, 0.83 mmol) over 5 min. On complete addition the mixture was quenched by addition of 1M sodium sulfite solution (2 ml) and the solvent removed in vacuo. The residue was treated with water (15 ml) and saturated sodium hydrogencarbonate solution (15 ml) and extracted with ethyl acetate (3×40 ml). The organics were combined then washed with brine (40 ml), dried over anhydrous sodium sulfate and evaporated to give an off white solid. This solid was purified by silica gel chromatography eluting with dichloromethane and 1% conc. ammonia on a gradient of methanol (1-2%) to give 3-bromo-7-methylimidazo[1,2-a]pyrimidine (100 mg, 63%) as a white crystalline solid: δH (400 MHz, CDCl3) 2.67 (3H, s), 6.87 (1H, d, J 7), 7.71 (1H, s), 8.27 (1H, d, J 7).

後処理

  1. additionOn complete addition the mixture
  2. customwas quenched by addition of 1M sodium sulfite solution (2 ml)
  3. customthe solvent removed in vacuo
  4. additionThe residue was treated with water (15 ml) and saturated sodium hydrogencarbonate solution (15 ml)
  5. extractionextracted with ethyl acetate (3×40 ml)
  6. washThe organics were combined then washed with brine (40 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. customto give an off white solid
  10. customThis solid was purified by silica gel chromatography
  11. washeluting with dichloromethane and 1% conc. ammonia on a gradient of methanol (1-2%)

出典と根拠

ORDレコード
ord-75fdc91a0f444d2191ac6562ef89bd33
出典データセット
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06642229B2

反応ノート

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