2,6-Lutidine → 5-(3-Cyanophenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-10-yl trifluoromethanesulfonate

HRID 2201186Notes

Reaction equation

HRID 2201186 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]([CH:35]=[CH:36][CH:37]=4)[C:33]#[N:34])=[C:21]2[C:20](=[O:39])[N:19]([CH3:40])[C:18]1=[O:41])[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:37]=[CH:36][CH:35]=[C:32]([C:33]#[N:34])[CH:31]=3)=[C:21]3[C:20](=[O:39])[N:19]([CH3:40])[C:18](=[O:41])[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-Lutidine2×HCID 67749Trifluoromethanesulfonic anhydride2×HCID 867234273-(1,3-Dimethyl-2,4,10-trioxo-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile

Product 1

HCID 867234285-(3-Cyanophenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-10-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoromethanesulfonic anhydride (221 μL, 1.31 mmol) was added to an ice-cooled solution of 3-(1,3-dimethyl-2,4,10-trioxo-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile (step 7) (350 mg, 1.01 mmol) and 2,6-lutidine (176 μL, 1.51 mmol) in DCM (5 mL). The solution was stirred at ice-bath temperature for 2 hours, further portions of 2,6-lutidine (88 μL, 0.78 mmol) and trifluoromethanesulfonic anhydride (85 μL, 0.50 mmol) were added. The reaction mixture was diluted with dichloromethane (40 mL) and was washed with water (2×20 mL) and sat. brine (1×20 mL). The organic phase was dried with magnesium sulfate and the solvent was removed under vacuum.

Workup

  1. washwas washed with water (2×20 mL) and sat. brine (1×20 mL)
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-a607d0486c0c4786801241212fcd33d0
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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