2,6-Lutidine → HCID 86723540, compound

HRID 2201308Notes

Reaction equation

HRID 2201308 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[N:28]([C:29]([C:30]4[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=4)=[C:21]2[C:20](=[O:38])[N:19]([CH3:39])[C:18]1=[O:40])[CH2:27][CH2:26][CH2:25][C:24]3=O.N1C(C)=CC=CC=1C>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:24]1[C:23]2[N:28]([C:29]([C:30]3[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=3)=[C:21]3[C:20](=[O:38])[N:19]([CH3:39])[C:18](=[O:40])[N:17]([CH3:16])[C:22]3=2)[CH2:27][CH2:26][CH:25]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydride2×HCID 86723539HCID 86723539, compound

Product 1

HCID 86723540HCID 86723540, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoromethanesulfonic anhydride (253 μL, 1.50 mmol) was added to an ice-cooled solution of 1,3-dimethyl-5-m-tolyl-8,9-dihydropyrimido[4,5-a]indolizine-2,4,10(1H,3H,7H)-trione (step 3) (388 mg, 1.15 mmol) and 2,6-lutidine (201 μL, 1.73 mmol) in DCM (7 mL). The solution was allowed to reach room temperature slowly and was stirred for 16 hours. A further portion of trifluoromethanesulfonic anhydride (39 μL, 0.23 mmol) was added and the solution was stirred for a further 30 minutes. The reaction mixture was diluted with dichloromethane (15 mL) and washed with water (2×8 mL) and sat brine (1×8 mL). The organic phase was dried with magnesium sulfate and the solvent was removed under vacuum, keeping the rotary evaporator water bath at 20° C. to give the title compound.

Workup

  1. customto reach room temperature
  2. stirringthe solution was stirred for a further 30 minutes
  3. washwashed with water (2×8 mL)
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. customthe solvent was removed under vacuum
  6. customthe rotary evaporator water bath at 20° C.

Sources & evidence

ORD record
ord-8296c65238c7408bafffa051de5d5068
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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