Tributylstannane → rac-Tert-butyl 7-hydroxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

HRID 517904Notes

Reaction equation

HRID 517904 reaction equation
S=C1O[CH:5]2[C:6]3[C:7]([N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27][CH:4]2[O:3]1)=[N:8][C:9]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)=[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[N:11]=3.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[OH:3][CH:4]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:7]2=[N:8][C:9]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[N:11]=[C:6]2[CH2:5]1

Participants

4

Reactant 2

HCID 5948Tributylstannane2×HCID 89690173HCID 89690173, compound

Product 1

HCID 89689748rac-Tert-butyl 7-hydroxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of tert-butyl 2-thioxo-7,8-di-p-tolyl-3a,4-dihydro-[1,3]dioxolo[41,51:4,5] pyrido[2,3-b]pyrazine-5(9bH)-carboxylate (step 3)(14 g, 28.6 mmol) in toluene (400 ml) was treated with tributyltin hydride (16.65 g, 57.2 mmol) and heated at reflux for 2 h. A further portion of tributyltin hydride (10 g) was added and refluxing continued for 6 h. The reaction mixture was left stirring over night at room temperature. The reaction mixture was evaporated to dryness and the iso-hexane (250 ml) was added to the residue. The suspension was stirred for 30 minutes at room temperature and then filtered. The solid was washed with iso-hexane (3×50 ml) to afford the titled compound;

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. temperaturerefluxing
  4. waitThe reaction mixture was left
  5. customThe reaction mixture was evaporated to dryness
  6. additionthe iso-hexane (250 ml) was added to the residue
  7. stirringThe suspension was stirred for 30 minutes at room temperature
  8. filtrationfiltered
  9. washThe solid was washed with iso-hexane (3×50 ml)

Sources & evidence

ORD record
ord-1955afcb353646ea9e86369342dceb2f
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

Loading…