Bromine → 3-Bromo-7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-alpha]pyrimidine

HRID 1796102ノート

反応式

HRID 1796102 の反応式
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][N:10]3[CH:13]=[CH:14][N:15]=[C:9]3[N:8]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[Br-:16].[K+].C([O-])(=O)C.[Na+].BrBr>CO>[Br:16][C:13]1[N:10]2[CH:11]=[CH:12][C:7]([CH2:6][N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[N:8][C:9]2=[N:15][CH:14]=1

参加物

6

反応物 4

HCID 24408BromineHCID 253877Potassium BromideHCID 517045Sodium AcetateHCID 695603727-([1,2,4]Triazol-1-ylmethyl)imidazo[1,2-alpha]pyrimidine

生成物 1

HCID 695598373-Bromo-7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-alpha]pyrimidine収率 97%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To 7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-α]pyrimidine (3.38 g, 16.9 mmol) in methanol (300 ml) saturated with potassium bromide was added sodium acetate (4.16 g, 50.7 mmol). This mixture was cooled (−10° C.) and bromine (2.70 g, 16.9 mmol) added dropwise over a five minute period. Stirring at this temperature was continued for 15 min before quenching the reaction with 5% (w/v) sodium sulphite solution (20 ml). Mixture was stirred for 15 min and methanol removed under reduced pressure. Residue was partitioned between dichloromethane (100 ml) and saturated sodium hydrogencarbonate solution (100 ml). Product was extracted into dichloromethane (4×100 ml) then the combined organic extracts were washed with brine (300 ml) and dried over anhydrous magnesium sulphate. Drying agent was removed by filtration and filtrate dried under reduced pressure to give 3-bromo-7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-α]pyrimidine (4.60 g, 97%) as a pale yellow solid: δH (360 MHz, d6-DMSO) 5.69 (2H, s), 7.06 (1H, d, J 7), 7.88 (1H, s), 8.05 (1H, s), 8.74 (1H, s), 8.80 (1H, d, J 7); m/z (ES+) 279, 281 (M++H).

後処理

  1. additionadded dropwise over a five minute period
  2. custombefore quenching
  3. customthe reaction with 5% (w/v) sodium sulphite solution (20 ml)
  4. stirringMixture was stirred for 15 min
  5. custommethanol removed under reduced pressure
  6. customResidue was partitioned between dichloromethane (100 ml) and saturated sodium hydrogencarbonate solution (100 ml)
  7. extractionProduct was extracted into dichloromethane (4×100 ml)
  8. washthe combined organic extracts were washed with brine (300 ml)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. customDrying agent
  11. customwas removed by filtration and filtrate
  12. customdried under reduced pressure

出典と根拠

ORDレコード
ord-c6bef84012ce4fb583456eb648b3f085
出典データセット
uspto-grants-2006_04
特許番号
US07030128B2

反応ノート

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