Lithium Bromide → HCID 86723441, compound

HRID 2201197Notes

Reaction equation

HRID 2201197 reaction equation
FC(F)(F)S(O[C:7]1[C:14]2[N:10]([C:11]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:12]3[C:18](=[O:19])[N:17]([CH3:20])[C:16](=[O:21])[N:15]([CH3:22])[C:13]3=2)[CH2:9][CH:8]=1)(=O)=O.[Br-].[Li+].C([Sn](CCCC)(CCCC)[C:38]1[O:39][C:40]([CH3:43])=[CH:41][CH:42]=1)CCC>C1COCC1.CCOCC>[CH3:22][N:15]1[C:13]2=[C:14]3[N:10]([C:11]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[C:12]2[C:18](=[O:19])[N:17]([CH3:20])[C:16]1=[O:21])[CH2:9][CH:8]=[C:7]3[C:38]1[O:39][C:40]([CH3:43])=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 82050Lithium BromideHCID 14024671Tributyl(5-methylfuran-2-yl)stannaneHCID 86723440HCID 86723440, compound

Product 1

HCID 86723441HCID 86723441, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,3-Dimethyl-2,4-dioxo-5-phenyl-2,3,4,7-tetrahydro-1H-pyrimido[4,5-a]pyrrolizin-9-yl trifluoromethanesulfonate (step 4) (100 mg, 0.227 mmol), Cul (4.31 mg, 0.023 mmol), lithium bromide (39.4 mg, 0.453 mmol), tributyl(5-methylfuran-2-yl)stannane (168 mg, 0.453 mmol) in THF (2 ml) and Pd-118 (14.77 mg, 0.023 mmol) were heated to reflux for 10 mins. The reaction mixture was filtered through a glass filter paper and the filtrate concentrated in vacuo. The crude product was dissolved in the minimum amount DCM/EtOAc and loaded onto a 12 g silica cartridge and eluted with 0-80% EtOAc in iso-hexane. The desired product was eluted at 30% EtOAc. The relevant fractions were combined and concentrated to yield a yellow solid. The isolated solid was suspended in Et2O and the solid filtered to yield the title product.

Workup

  1. temperatureto reflux for 10 mins
  2. filtrationThe reaction mixture was filtered through a glass
  3. filtrationfilter paper
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe crude product was dissolved in the minimum amount DCM/EtOAc
  6. washeluted with 0-80% EtOAc in iso-hexane
  7. washThe desired product was eluted at 30% EtOAc
  8. concentrationconcentrated
  9. customto yield a yellow solid
  10. filtrationthe solid filtered

Sources & evidence

ORD record
ord-20c2e21319254a10b47d525bfc38f7dd
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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