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

HRID 482208

Reaction equation

HRID 482208 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-129bbeee9d4447a4b6c0c6bf66653791
Source dataset
uspto-grants-1998_08
Patent number
US05795756

Linked notes

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