Bromobenzene → ethyl (E)-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

HRID 1828514Notes

Reaction equation

HRID 1828514 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].CN([CH:21]=[C:22]([C:30](OCC)=[O:31])[CH:23]=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])C.BrC1C=CC=CC=1>>[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]3[C:30](=[O:31])[C:22](/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][N:17]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 7961BromobenzeneHCID 220636524-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-2-aminopyridineHCID 54366534Diethyl 1-dimethylamino-1,3-butadiene-2,4-dicarboxylate

Product 1

HCID 86588142ethyl (E)-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoateYield 6.2%

Conditions

Temperature
160 °C

Procedure

4-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-2-aminopyridine(200 mg), diethyl 4-dimethylaminomethyleneglutaconate (265 mg) was added with bromobenzene (2 ml) and heated at 120° C. for 1 hour and at 160° C. for 4 hours with stirring. The residue was purified by silica gel column chromatography to obtain the title compound (20 mg) as white powder.

Workup

  1. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8e1ee26a48b34949bd410e20598ecf71
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

Loading…