Potassium Carbonate → 9-(4-benzoylbenzyl)-6-chloro-9H-purine

HRID 366980

反応式

HRID 366980 の反応式
[C:1]([C:9]1[CH:25]=[CH:24][C:12]([CH2:13][N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][CH:17]=[N:18][C:19]=3N)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26]C1N=CN=C2C=1NC=N2.C(C1C=CC(CCl)=CC=1)(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:1]([C:9]1[CH:25]=[CH:24][C:12]([CH2:13][N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][CH:17]=[N:18][C:19]=3[Cl:26])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 30163764-(Chloromethyl)benzophenoneHCID 53592776-ChloropurineHCID 99055279-(4-Benzoylbenzyl)-9H-adenine

生成物 1

HCID 232873809-(4-benzoylbenzyl)-6-chloro-9H-purine収率 41%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

The synthesis of 9'-(4-benzoylbenzyl)-9H-adenine (20) was achieved by the following procedure (Scheme 9). A mixture of 6-chloropurine (3.09 g, 20 mmol), 4-benzoyl-benzyl chloride (6.05 g, 22 mmol) and K2CO3 (3.04 g, 22 mmol) in DMF (50 ml) was stirred overnight at rt, diluted with water (400 ml), and extracted with EtOAc (3×100 ml) (Scheme 9)52. The combined organic layers were washed with water and brine, dried over MgSO4, concentrated in vacuo, and subjected to flash-chromatography on silica gel eluting with CH2Cl2 -acetone (80:20). The fractions containing the higher Rf, the major component, were combined and concentrated in vacuo to give 2.86 g (41%) of 9-(4-benzoylbenzyl)-6-chloro-9H-purine. To a solution of this iminochloride (1.05 g, 3 mmol) in EtOH (20 ml) was added a 2M solution of NH3 in MeOH. This medium was warmed overnight at 90° C. under pressure (constant volume). It was then cooled and concentrated in vacuo. The residue was washed successively with a 1M solution of NaHCO3, water, iPrOH, and hot CH2Cl2, and then was recrystallized from butanol to give 0.53 g (54%) of 9-(4-benzoylbenzyl)-9H-adenine (20). 1H NMR (DMSO) δ 5.49 (s, 2H, CH2), 7.27-7.71 (m, 9H, H--Ar), 8.15 (s, 1H, H-2), 8.30 (s, 1H, H-8). ##STR10## Synthesis of 9-[(4-bis-phenyl)buten-4-yl]-9H-adenine (21)

後処理

  1. extractionextracted with EtOAc (3×100 ml) (Scheme 9)52
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. additionThe fractions containing the higher Rf
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-04be9eb3513647a4b43e23caf5eb65e2
出典データセット
uspto-grants-2000_10
特許番号
US06132957

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