2,6-Lutidine → HCID 86723435, compound

HRID 2201192Notes

Reaction equation

HRID 2201192 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][N:17]1[C:22]2=[C:23]3[C:28](=O)[CH2:27][CH2:26][NH:25][N:24]3[C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:21]2[C:20](=[O:37])[N:19]([CH3:38])[C:18]1=[O:39].N1C(C)=CC=CC=1C>C(Cl)Cl>[CH3:16][N:17]1[C:18](=[O:39])[N:19]([CH3:38])[C:20](=[O:37])[C:21]2[C:22]1=[C:23]1[N:24]([C:30]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[NH:25][CH2:26][CH:27]=[C:28]1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86723434HCID 86723434, compound

Product 1

HCID 86723435HCID 86723435, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.254 ml, 1.506 mmol) was added slowly to a solution of 1,3-dimethyl-5-phenyl-8,9-dihydropyrimido[4′,5′:3,4]pyrrolo[1,2-b]pyridazine-2,4,10(1H,3H,7H)-trione (step 4) (222 mg, 0.684 mmol) and 2,6-lutidine (commercial) (0.159 ml, 1.369 mmol) in DCM (10 ml) at 0° C. and the mixture stirred for 1.75 hours. The reaction mixture was quenched with sat. NaHCO3(aq) and extracted with DCM. The organic phase was passed through a hydrophobic frit and evaporated under reduced pressure. Purification of the residue by chromatography on silica, eluting with 20% EtOAc/hexane then 40% EtOAc/hexane afforded the title compound as a yellow solid.

Workup

  1. customThe reaction mixture was quenched with sat. NaHCO3(aq)
  2. extractionextracted with DCM
  3. customevaporated under reduced pressure
  4. customPurification of the residue by chromatography on silica
  5. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-8620eed6a27943dca2e34b915bf9d88f
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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