Acetic Anhydride → tert-Butyl-7-acetoxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

HRID 517905Notes

Reaction equation

HRID 517905 reaction equation
[OH:1][CH:2]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[N:9]=[C:4]2[CH2:3]1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>N1C=CC=CC=1>[C:29]([O:28][C:26]([N:24]1[C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[N:9]=[C:4]2[CH2:3][CH:2]([O:1][C:33](=[O:35])[CH3:34])[CH2:25]1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 89689748rac-Tert-butyl 7-hydroxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Product 1

HCID 89690147tert-Butyl-7-acetoxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of tert-butyl 7-hydroxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 4) (500 mg, 1.159 mmol) in pyridine (3 ml) was treated slowly with acetic anhydride (0.219 ml, 2.317 mmol) and the resulting yellow solution was stirred at room temperature overnight. The reaction mixture was evaporated to dryness and purification of the crude material by chromatography on silica eluting with 0-60% EtOAc in iso-hexane afforded the titled compound;

Workup

  1. customThe reaction mixture was evaporated to dryness and purification of the crude material by chromatography on silica eluting with 0-60% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-cd3e657e1d1146049c19938a92e7ed41
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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