Water → 8-(3-Aminoazepan-1-yl)-3-methyl-7-(2-methylbenzyl)-3,7-dihydropurine-2,6-dione

HRID 458641Notes

Reaction equation

HRID 458641 reaction equation
Br[C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:9]2[C:8](=[O:19])[NH:7][C:6](=[O:20])[N:5]([CH3:21])[C:4]=2[N:3]=1.[NH:22]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]([NH2:29])[CH2:23]1.C(N(CC)CC)C.O>CS(C)=O.ClCCl>[NH2:29][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][N:22]([C:2]2[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[C:9]3[C:8](=[O:19])[NH:7][C:6](=[O:20])[N:5]([CH3:21])[C:4]=3[N:3]=2)[CH2:23]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2756445Azepan-3-amineHCID 225086008-Bromo-3-methyl-7-(2-methylbenzyl)-3,7-dihydropurine-2,6-dione

Product 1

HCID 225086168-(3-Aminoazepan-1-yl)-3-methyl-7-(2-methylbenzyl)-3,7-dihydropurine-2,6-dione

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

8-Bromo-3-methyl-7-(2-methylbenzyl)-3,7-dihydropurine-2,6-dione (82A) (300 mg, 0,86 mmol) and azepan-3-ylamine (294 mg, 2,6 mmol), and triethylamine (0.6 ml, 4.3 mmol) were dissolved in 3 ml of DMSO and the mixture was subjected to microwaves (method F, 200° C., 300 W) for 3 minutes. To the reaction mixture was added 100 ml of water and 100 ml of dichloromethane, and the organic layer was washed with 1N NaOH, and dried over sodium sulfate. The solvents were evaporated and the crude product was purified by preparative HPLC (method A1, Rt=6.93 min.). Evaporation of the solvent afforded the title compound as yellow crystals.

Workup

  1. washthe organic layer was washed with 1N NaOH
  2. dry with materialdried over sodium sulfate
  3. customThe solvents were evaporated
  4. customthe crude product was purified by preparative HPLC (method A1, Rt=6.93 min.)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-cc7586c4650940ff96a58e419c2b22aa
Source dataset
uspto-grants-2007_03
Patent number
US07192952B2

Reaction notes

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