HCID 69013579, compound → HCID 178501831, compound

HRID 1297152Notes

Reaction equation

HRID 1297152 reaction equation
[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[C:17]([O:25]CC)=[CH:18][C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[C:17](=[O:25])[CH:18]=[C:19]([OH:24])[C:20]([O:22][CH3:23])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 69013579HCID 69013579, compound

Product 1

HCID 178501831HCID 178501831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 4-(9-benzyl-9H-purin-6-yl)-4-ethoxy-2-oxo-but-3-enoate (9) (100 mg, 0.20 mmole) obtained in above step was stirred at room in CH2Cl2 (20 mL) and treated with FeCl3.6H2O (0.125 g, 0.40 mmole). The reaction mixture was stirred at 40° C. for 5 h. Chloroform was distilled off and the resulting residue was treated with 1 N HCl (50 mL) for 1 h and then extracted with EtOAc (4×20 mL). The extract was dried over anhydrous sodium sulfate and the EtOAc distilled off to give a brownish residue which was purified by ion exchange chromatography (diethylamino sephadex anion exchange resin, CH3CN:H2O, (1:1) eluent). Yield 5.2 mg. Mp 166-167° C. 1H NMR (CDCl3) δ 3.99 (s, 3H, CH3), 5.54 (s, 2H, benzylic CH2), 7.35-7.41 (m, 5H, aromatic), 7.9 (s, 1H, olefinic CH), 8.3 (s,1H, purine C8—H), 9.19 (s,1H, purine C2—H). 13C NMR (CDCl3) δ 47.7, 53.4, 101.4, 128.0, 128.0, 128.9, 129.3, 131.8, 134.5, 147.4, 152.3, 154.3, 162.1, 172.8, and 185.7. FAB-HRMS: [M+H]+ calcd. for C17H15N4O4 339.1093, found 339.1083.

Workup

  1. distillationChloroform was distilled off
  2. additionthe resulting residue was treated with 1 N HCl (50 mL) for 1 h
  3. extractionextracted with EtOAc (4×20 mL)
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe EtOAc distilled off
  6. customto give a brownish residue which
  7. customwas purified by ion exchange chromatography (diethylamino sephadex anion exchange resin, CH3CN:H2O, (1:1) eluent)

Sources & evidence

ORD record
ord-e748682f7903495faf9fb91ae91d6273
Source dataset
uspto-grants-2007_07
Patent number
US07250421B2

Reaction notes

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