Phenol → 8-(3-Aminoazepan-1-yl)-7-benzyl-1,3-dimethyl-3,7-dihydropurine-2,6-dione

HRID 984818Notes

Reaction equation

HRID 984818 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]([CH3:20])[C:11]=2[N:10]=[C:9]1[N:21]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]([NH:28]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(O)C=CC=CC=1.CCOC(C)=O>Br.C1C=CC=CC=1>[NH2:28][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][N:21]([C:9]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]3[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]([CH3:20])[C:11]=3[N:10]=2)[CH2:22]1

Participants

6

Reactant 3

HCID 996PhenolHCID 8857Ethyl AcetateHCID 22508573N-(1-(7-Benzyl-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-8-yl)azepan-3-yl)-4-methylbenzenesulfonamide

Product 1

HCID 101345098-(3-Aminoazepan-1-yl)-7-benzyl-1,3-dimethyl-3,7-dihydropurine-2,6-dione

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 260Hydrogen BromideSolvent

Procedure

N-(1-(7-Benzyl-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-8-yl)azepan-3-yl)-4-methylbenzenesulfonamide (6C) (100 mg, 0.19 mmol) was dissolved in hydrobromic acid (48%, 5 ml) and benzene (0.07 ml), and phenol (61.4 mg, 0.65 mmol) was added. The mixture was heated to reflux for three hours, and after cooling 20 ml of EtOAc was added. The layers were separated, and the aqueous layer washed with 20 ml of EtOAc. pH was adjusted to 11 with 10M sodium hydroxide. The aqueous layer was extracted with diethyl ether (3×20 ml), and the combined organic layers were dried over sodium sulphate and the solvent was evaporated. The crude product was dissolved in 5 ml of DCM and 0.5 ml of trifluoroacetic acid was added. The solvents were evaporated and the crude product was purified by preparative HPLC (method A1, Rt=7.63 min). Evaporation of the solvent gave the title compound as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for three hours
  3. additionwas added
  4. customThe layers were separated
  5. washthe aqueous layer washed with 20 ml of EtOAc
  6. extractionThe aqueous layer was extracted with diethyl ether (3×20 ml)
  7. dry with materialthe combined organic layers were dried over sodium sulphate
  8. customthe solvent was evaporated
  9. dissolutionThe crude product was dissolved in 5 ml of DCM
  10. addition0.5 ml of trifluoroacetic acid was added
  11. customThe solvents were evaporated
  12. customthe crude product was purified by preparative HPLC (method A1, Rt=7.63 min)
  13. customEvaporation of the solvent

Sources & evidence

ORD record
ord-daa9c3ca060c420fbe25ca700d3b5cdb
Source dataset
uspto-grants-2005_03
Patent number
US06869947B2

Reaction notes

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