Hydrogen Bromide → (+/-)-9-Amino-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-5H-1,4a,7-triaza-benzocyclohepten-4-one dihydrobromide

HRID 1890400Notes

Reaction equation

HRID 1890400 reaction equation
C(OC([N:6]1[CH2:12][CH:11]([NH2:13])[C:10]2=[N:14][C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)=[CH:16][C:17](=[O:18])[N:9]2[CH2:8][CH2:7]1)=O)C.[BrH:25]>C(O)(=O)C>[BrH:25].[BrH:25].[NH2:13][CH:11]1[C:10]2=[N:14][C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)=[CH:16][C:17](=[O:18])[N:9]2[CH2:8][CH2:7][NH:6][CH2:12]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 669298339-amino-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4-a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester

Product 1

HCID 68731596(+/-)-9-Amino-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-5H-1,4a,7-triaza-benzocyclohepten-4-one dihydrobromideYield 125.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 9.70 g (23.59 mmol) of (+/−)-9-amino-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester (step 1.4) dissolved in 118 mL of glacial acetic acid was added 41.38 mL (235.86 mmol) of hydrobromic acid (33 wt % solution in glacial acetic acid). The resulting mixture was stirred at 90° C. for 16 hours, cooled and evaporated to dryness. Toluene was added to the residue and evaporated. Ethanol was added to the residue and evaporated. The crude was triturated with diethyl ether and filtered to afford 12.40 g of the product as a brown powder.

Workup

  1. temperaturecooled
  2. customevaporated to dryness
  3. additionToluene was added to the residue
  4. customevaporated
  5. additionEthanol was added to the residue
  6. customevaporated
  7. customThe crude was triturated with diethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-632c5309b1a741eba52eb6ca86f4ec7d
Source dataset
uspto-grants-2013_08
Patent number
US08507475B2

Reaction notes

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