Ammonium cerium-nitrate → 9-amino-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4-a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester

HRID 1890421Notes

Reaction equation

HRID 1890421 reaction equation
C(#N)C.[CH2:4]([O:6][C:7]([N:9]1[CH2:15][CH:14]([NH:16]CC2C=CC(OC)=CC=2)[C:13]2=[N:26][C:27]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][N:32]=3)=[CH:28][C:29](=[O:30])[N:12]2[CH2:11][CH2:10]1)=[O:8])[CH3:5].O.[N+]([O-])([O-])=O.[Ce].[NH4+]>>[CH2:4]([O:6][C:7]([N:9]1[CH2:15][CH:14]([NH2:16])[C:13]2=[N:26][C:27]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][N:32]=3)=[CH:28][C:29](=[O:30])[N:12]2[CH2:11][CH2:10]1)=[O:8])[CH3:5]

Participants

3

Reactant 2

HCID 57418452Ammonium cerium-nitrate2×HCID 866498749-(4-methoxy-benzylamino)-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester acetonitrile water

Product 1

HCID 669298339-amino-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4-a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl esterYield 65.3%

Procedure

To a solution of 10.75 g (23.86 mmol) of 9-(4-methoxy-benzylamino)-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester acetonitrile/water (160/80 mL) was added 26.16 g (47.73 mmol) of ammonium cerium nitrate. The reaction was stirred at room temperature for 2 hours. 13.08 g (23.86 mmol) of ammonium cerium nitrate was added and the reaction was stirred at room temperature for 0.5 hours. After an acido-basic work-up and extraction with dichloromethane, the organic phase was washed with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated to afford 5.15 g (65%) of a powder.

Workup

  1. stirringthe reaction was stirred at room temperature for 0.5 hours
  2. extractionAfter an acido-basic work-up and extraction with dichloromethane
  3. washthe organic phase was washed with a saturated solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac3a288d485a424088a8389dedbfdf5d
Source dataset
uspto-grants-2013_08
Patent number
US08507476B2

Reaction notes

Loading…