Morpholine → tert-Butyl (E)-3-{8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

HRID 1828485Notes

Reaction equation

HRID 1828485 reaction equation
[CH:1]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:41]=[CH:40][N:14]3[C:15](=[O:39])[C:16](/[CH:30]=[CH:31]/[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[C:17](OS(C4C=CC(C)=CC=4)(=O)=O)[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1>CN(C)C=O>[CH:1]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:41]=[CH:40][N:14]3[C:15](=[O:39])[C:16](/[CH:30]=[CH:31]/[C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])=[C:17]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86588115tert-Butyl (E)-3-[8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-{[(4-methyl-phenyl)sulfonyl]oxy)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoate2×

Product 1

HCID 86588116tert-Butyl (E)-3-{8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoateYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The tert-butyl (E)-3-{8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-{[(4-methylphenyl)sulfonyl]oxy}-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (9.0 mg, 0.0152 mmol) obtained in (A) was dissolved in dimethylformamide (0.75 ml), added with morpholine (13.2 μl, 0.152 mmol), and stirred overnight at room temperature. The reaction mixture was concentrated, and then the residue was purified by thin layer chromatography (n-hexane:ethyl acetate=1:1, v/v) to obtain the title compound (6.7 mg, 87%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by thin layer chromatography (n-hexane

Sources & evidence

ORD record
ord-28ef69e6f11549098bd010b6c6a0b92e
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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