Tetra-n-butylammonium tribromide → HCID 86727335, compound

HRID 518983Notes

Reaction equation

HRID 518983 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][C:10]1[N:5]2[CH:6]([CH3:17])[C:7](=[O:16])[NH:8][N:9]=1.[Br-:18].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>CO.C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[Br:18])[O:12][CH2:11][C:10]1[N:5]2[CH:6]([CH3:17])[C:7](=[O:16])[NH:8][N:9]=1

Participants

5

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 867272916-Amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

Product 1

HCID 86727335HCID 86727335, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a 30° C. solution of 6-amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Preparation #2, Step E, 3.0 g, 12.92 mmol) in MeOH (15 mL) and DCM (7.5 mL) was added tetrabutylammonium tribromide (3.31 g, 12.92 mmol) in portions and the resulting black solution was stirred for 1 h. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1-50% EtOAc in petroleum ether) to give 6-amino-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (1.2 g, 3.86 mmol, 30%). LC/MS (Table 1, Method 4) Rt=1.337 min.; MS m/z: 311/313 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography on silica gel (eluting with 1-50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-08d7bf6e513e4df2b976c0b7ed5fdbc2
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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