Morpholine → 2-(Ethyl(methyl)amino)-4-methyl-6-morpholino-pyridine-3-carboxylic acid ethylester

HRID 922041Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:14]([CH2:16][CH3:17])[CH3:15])=[N:8][C:9](Cl)=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>[OH-].[Na+].CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:14]([CH2:16][CH3:17])[CH3:15])=[N:8][C:9]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 4.0 g (15.6 mmol) 6-chloro-2-(ethyl(methyl)amino)-4-methyl-pyridine-3-carboxylic acid ethylester and 13.6 ml (155.8 mmol) morpholine was heated in the MW to 135° C. for 2 h. Then the mixture was diluted with a 1M aq. NaOH sol. and EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 2.0 g (6.4 mmol, 41%) 2-(ethyl(methyl)amino)-4-methyl-6-morpholino-pyridine-3-carboxylic acid ethylester.

Workup

customThe organic layer was separated
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification of the residue by CC (hexane/EtOAc 9:1)

Sources & evidence

ORD record: ord-6bb2cde97d234e959d8a17b2fdc49199
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278103B2

Reaction notes

Loading…