Boron trifluoride etherate → 1-Methyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxide

HRID 513687Notes

Reaction equation

HRID 513687 reaction equation
[CH2:1](OCC)C.FB(F)F.[CH:10]1[C:23]2[CH:22]=[CH:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[NH:13][S:12](=[O:25])(=[O:24])[N:11]=1.C[Li]>C1COCC1>[CH3:1][CH:10]1[C:23]2[CH:22]=[CH:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[NH:13][S:12](=[O:25])(=[O:24])[NH:11]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 681833864H-3-Thia-2,4,5-triaza-phenanthrene 3,3-dioxideHCID 178418348HCID 178418348, compound

Product 1

HCID 681832981-Methyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxideYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethoxyethane—trifluoroborane (1:1; 32.3 μl, 0.26 mmol) was added dropwise to a solution of 4H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxide 406 (60 mg, 0.26 mmol) in dry THF (3 ml) under an atmosphere of N2. The mixture was stirred at room temperature for 1 h and then cooled to −78° C. Methyllithium (1.6M in Et2O; 1.61 ml, 2.57 mmol) was added dropwise and the mixture was stirred −78° C. for 1 h. The reaction was quenched with sat NH4Cl (2 ml) at -78° C. and the mixture was warmed to room temperature. The mixture was extracted with EtOAc and the residue was purified by preparative HPLC (acidic conditions 1) to give the title compound (18 mg, 28%).

Workup

  1. temperaturecooled to −78° C
  2. stirringthe mixture was stirred −78° C. for 1 h
  3. customThe reaction was quenched with sat NH4Cl (2 ml) at -78° C.
  4. temperaturethe mixture was warmed to room temperature
  5. extractionThe mixture was extracted with EtOAc
  6. customthe residue was purified by preparative HPLC (acidic conditions 1)

Sources & evidence

ORD record
ord-0bedb2d0d9f34f26a43338d626b5b1a0
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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