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

HRID 1796102노트

반응식

HRID 1796102 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c6bef84012ce4fb583456eb648b3f085
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030128B2

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