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Bromine → 8-Bromo-2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine

HRID 2111657
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HRID 2111657 반응식
[Br:1]Br.C([O-])(=O)C.[Na+].[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH2:22][C:23]2[CH:24]=[N:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[C:15]([NH2:30])[N:14]=1)[CH2:9][CH2:10][CH3:11]>C(O)(=O)C>[Br:1][C:18]1[N:19]([CH2:22][C:23]2[CH:24]=[N:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[C:20]2[C:16]([N:17]=1)=[C:15]([NH2:30])[N:14]=[C:13]([O:12][CH2:8][CH2:9][CH2:10][CH3:11])[N:21]=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 229289322-Butoxy-9-(6-chloro-3-pyridylmethyl)adenine

생성물 1

HCID 229289138-Bromo-2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine수율 62.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Potassium carbonate (2.85 g, 20.6 mmol) and 2-chloro-5-chloromethylpyridine (3.33 g, 20.6 mmol) were added to the DMF solution (125 ml) of 2-butoxyadenine (2.60 g, 12.5 mmol) obtained in Reference Example 1. The resultant was stirred while heating at 80° C. for 2.5 hours. The reaction solution was concentrated under reduced pressure, water (100 ml) was added thereto, and the resultant was neutralized with 1N hydrochloric acid. The precipitated solid was collected by filtration. The resulting solid was dissolved in methylene chloride (100 ml), hexane (150 ml) was added under ice cooling, and the precipitated crystal was collected by filtration. Thus, 2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine was obtained (yield: 3.12 g). Bromine (1.92 ml, 37.5 mmol) was added to an acetic acid suspension (186 ml) comprising sodium acetate (3.05 g, 37.2 mmol) and 2-butoxy-9-(6-chloro-3-pyridylmethyl)adenine (3.1 g, 9.31 mmol) at room temperature, and the resultant was allowed to react for 4 hours. The reaction solution was removed by distillation under reduced pressure, water (200 ml) was added to the residue, and the resultant was neutralized with 5N sodium hydroxide under ice cooling. The precipitated crystal was collected by filtration, and crude crystal was recrystalized with the aid of methanol. The resultant was dried under reduced pressure at 40° C. for 15 hours. Thus, 2.38 g of the title compound was obtained as a white powdery crystal (yield: 62%).

후처리

  1. customat room temperature
  2. customto react for 4 hours
  3. customThe reaction solution was removed by distillation under reduced pressure, water (200 ml)
  4. additionwas added to the residue
  5. filtrationThe precipitated crystal was collected by filtration
  6. customcrude crystal was recrystalized with the aid of methanol
  7. customThe resultant was dried under reduced pressure at 40° C. for 15 hours

출처 및 근거

ORD 기록
ord-ee9e12cb61e944e9a2356133ebac47ea
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07521454B2

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