Trichlorophenyl malonate → 2-Hydroxy-8-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1828430Notes

Reaction equation

[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][O: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].[C:18](OC1C=CC(Cl)=C(Cl)C=1Cl)(=[O:23])[CH2:19][C:20]([O-])=[O:21]>C1(C)C(C)=CC=CC=1>[OH:23][C:18]1[N:17]=[C:13]2[CH:12]=[C:11]([O:10][CH2:9][C:6]3[S:7][CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=3)[CH:16]=[CH:15][N:14]2[C:20](=[O:21])[CH:19]=1

Participants

Conditions

Temperature: 140 °C

Procedure

4-[(4-Isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridinamine (378 mg, 1.52 mmol) dissolved in xylene (15 ml) was added with trichlorophenyl malonate (750 mg, 1.62 mmol) and refluxed by heating at 140° C. for 1 hour and 30 minutes. The reaction solution was returned to room temperature and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=100:1→80:1→50:1) to obtain 307 mg (64%) of the title compound.

Workup

temperaturerefluxed
customwas returned to room temperature
concentrationconcentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=100:1→80:1→50:1)

Sources & evidence

ORD record: ord-be80716bf766462ba1794a8474bf675a
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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