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

HRID 1371462
ノート
印刷プレビュー

反応式

HRID 1371462 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-94f04619dd5d470baf0f83076efb6abf
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07157465B2

反応ノート

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