Adenine → 9-(Phenylmethyl)-9H-purin-6-amine

HRID 1297150

反応式

HRID 1297150 の反応式
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 190AdenineHCID 7498Benzyl BromideHCID 24758Sodium hydride

生成物 1

HCID 202629-(Phenylmethyl)-9H-purin-6-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a suspension of adenine (5) (5.00 g, 37.0 mmol) in dry DMF (120 mL) was added NaH (1.77 g, 44.4 mmol) at room temperature. The reaction mixture was stirred for 30 min and the resulting white suspension was warmed to 60° C. for an additional 30 min. Benzyl bromide (7.59 g, 44.4 mmol) was added and the mixture was stirred for 24 h at 60° C. TLC of the reaction mixture indicated the formation of two products. DMF was distilled off under reduced pressure and the resulting residue was treated with water (20 mL). The white solid that separated out, was filtered and dried under vacuum. Separation and purification was through flash column chromatography using CHCl3::MeOH (9:1) for elution. 9-Benzyladenine: yield 5.5 g. (66%); mp 231-232° C.; 1H NMR (DMSO-d6,: δ 5.38 (s, 2H, CH2), 7.29-7.33 (m, 7H, Ar—H and NH2), 8.17 (s, 1H, purine C8—H), 8.28 (s, 1H, purine C2—H). 7-Benzyladenine: yield 1.8 g. (21%). Mp 252-255° C. 1H NMR (DMSO-d6): δ 5.53 (s, 2H, CH2), 7.29-7.48 (m, 5H, Ar—H), 7.81 (s, 1H, purine C8—H), 8.0-8.1 (br, 2H, NH2), 8.6 (s, 1H, purine C2—H).

後処理

  1. stirringthe mixture was stirred for 24 h at 60° C
  2. distillationDMF was distilled off under reduced pressure
  3. additionthe resulting residue was treated with water (20 mL)
  4. customThe white solid that separated out
  5. filtrationwas filtered
  6. customdried under vacuum
  7. customSeparation and purification
  8. washMeOH (9:1) for elution

出典と根拠

ORDレコード
ord-876262c0be254120ba2da76ee0d52dbc
出典データセット
uspto-grants-2007_07
特許番号
US07250421B2

関連ノート

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