Potassium Carbonate → HCID 9801004, compound

HRID 1767449Notes

Reaction equation

HRID 1767449 reaction equation
[NH:1]1[CH2:7][CH:6]([CH2:8][OH:9])[CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:10]([N:17]1[C:25]2[C:24](=[O:26])[N:23]([CH3:27])[C:22](=[O:28])[N:21]([CH3:29])[C:20]=2[N:19]=[C:18]1Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:10]([N:17]1[C:25]2[C:24](=[O:26])[N:23]([CH3:27])[C:22](=[O:28])[N:21]([CH3:29])[C:20]=2[N:19]=[C:18]1[N:1]1[CH2:7][CH:6]([CH2:8][OH:9])[CH2:5][NH:4][CH2:3][CH2:2]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3253727-Benzyl-8-chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dioneHCID 23090161(1,4-Diazepan-6-yl)methanol

Product 1

HCID 9801004HCID 9801004, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

([1,4]Diazepan-6-yl)methanol (1C) including potassium carbonate salts (ca 1 mmol) was suspended in dry DMF (200 ml) and 7-benzyl-8-chloro-1,3-dimethyl-3,7-dihydro-purine-2,6-dione (199.9 mg, 0.656 mmol) and potassium carbonate (453 mg, 3.28 mmol) were added. The reaction mixture was stirred at room temperature for 24 hours, heated to 60° C. for 3 hours, heated to 95° C. for 5 hours and heated to 120° C. for 2 hours. The suspension was allowed to cool to room temperature and white salts were filtered off. The filtrate was evaporated and purified by chromatography on silica, using 5% methanol in dichloromethane as the eluent. Fractions containing the product were evaporated and purified by preparative HPLC (method A2; Rt=2.52 min.) to afford 8 mg of the title compound as an yellow oil in 1% yield.

Workup

  1. temperatureheated to 60° C. for 3 hours
  2. temperatureheated to 95° C. for 5 hours
  3. temperatureheated to 120° C. for 2 hours
  4. temperatureto cool to room temperature
  5. filtrationwhite salts were filtered off
  6. customThe filtrate was evaporated
  7. custompurified by chromatography on silica
  8. additionFractions containing the product
  9. customwere evaporated
  10. custompurified by preparative HPLC (method A2; Rt=2.52 min.)

Sources & evidence

ORD record
ord-e8729dc5a87744e685921b6c469e6d69
Source dataset
uspto-grants-2007_06
Patent number
US07235538B2

Reaction notes

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