Ammonia → HCID 68626960, compound

HRID 1890239Notes

Reaction equation

HRID 1890239 reaction equation
Br[CH:2]1[C:8]2=[N:9][C:10]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][N:15]=3)=[CH:11][C:12](=[O:13])[N:7]2[CH2:6][CH2:5][O:4][CH2:3]1.[NH3:20]>>[NH2:20][CH:2]1[C:8]2=[N:9][C:10]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][N:15]=3)=[CH:11][C:12](=[O:13])[N:7]2[CH2:6][CH2:5][O:4][CH2:3]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 68626997(+/-)-9-Bromo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4-a-diaza-benzocyclohepten-4-one

Product 1

HCID 68626960HCID 68626960, compoundYield 44%

Conditions

Temperature
100 °C

Procedure

A suspension of 18.7 g (57.89 mmol) of (+/−)-9-bromo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4a-diaza-benzocyclohepten-4-one in 520 mL of ammonia (7N solution in MeOH) in sealed tubes was stirred at 100° C. for 4 hours. The cooled solution was evaporated to remove solvent. After an acido-basic work-up and extraction with dichloromethane, the mixture was washed with saturated solution of sodium chloride. The organic phase was dried over sodium sulfate and concentrated. The residue was organised in diethyl ether to afford 6.70 g (44%) of product as a yellow solid.

Workup

  1. customThe cooled solution was evaporated
  2. customto remove solvent
  3. extractionAfter an acido-basic work-up and extraction with dichloromethane
  4. washthe mixture was washed with saturated solution of sodium chloride
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dccb9c530f154c7c8322ad6f741de69f
Source dataset
uspto-grants-2013_08
Patent number
US08507470B2

Reaction notes

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