Water → HCID 53960330, compound

HRID 1608554Notes

Reaction equation

HRID 1608554 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[NH:5][C:4](=[O:12])[C:3]=1[NH:13][C:14]([C:16]12[CH2:23][CH:22]3[CH2:24][CH:18]([CH2:19][CH:20]1[CH2:21]3)[CH2:17]2)=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33](=[O:35])[CH3:34].O>CN(C)C=O>[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:32][C:33](=[O:35])[CH3:34])[C:4](=[O:12])[C:3]=1[NH:13][C:14]([C:16]12[CH2:17][CH:18]3[CH2:24][CH:22]([CH2:21][CH:20]1[CH2:19]3)[CH2:23]2)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11715BromoacetoneHCID 54472978HCID 54472978, compound

Product 1

HCID 53960330HCID 53960330, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.20 g (6.63 mmol) of 6-amino-5-(3-tricyclo[3.3.1.03,7 ]nonylcarbonylamino)-1-propyluracil (Japanese Published Unexamined Patent Application No. 173889/91) in 35 ml of dimethylformamide, 3.24 g (9.95 mmol) of cesium carbonate, 1.23 ml (13.3 mmol) of bromoacetone were added with stirring. The reaction mixture was stirred at 60° C. for 3.5 hours. The mixture was cooled, poured into 100 ml of water and extracted three times with 30 ml of chloroform. The organic layer was washed with 0.2M sodium thiosulfate aqueous solution, with water, with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluate: 2% methanol/chloroform) to give 1.70 g (yield 66%) of Compound I as a pale yellow powder.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 3.5 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted three times with 30 ml of chloroform
  4. washThe organic layer was washed with 0.2M sodium thiosulfate aqueous solution, with water, with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluate: 2% methanol/chloroform)

Sources & evidence

ORD record
ord-eebd031402004bfa8f5836c23e311372
Source dataset
uspto-grants-1995_03
Patent number
US05395836

Reaction notes

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