4-[2-(4-Ethyl-1,3-thiazol-2-yl)ethyl]-2-pyridinamine → 8-[2-(4-Ethyl-1,3-thiazol-2-yl)ethyl]-2-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1828421Notes

Reaction equation

[CH2:1]([C:3]1[N:4]=[C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[CH:11]=2)[S:6][CH:7]=1)[CH3:2].[C:17](OC1C=CC(Cl)=C(Cl)C=1Cl)(=[O:22])[CH2:18][C:19]([O-])=[O:20]>C1(C)C(C)=CC=CC=1>[CH2:1]([C:3]1[N:4]=[C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]3[C:19](=[O:20])[CH:18]=[C:17]([OH:22])[N:16]=[C:12]3[CH:11]=2)[S:6][CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

4-[2-(4-Ethyl-1,3-thiazol-2-yl)ethyl]-2-pyridinamine (480 mg, 2.044 mmol) dissolved in xylene (10 ml) was added with trichlorophenyl malonate (1 g, 2.160 mmol) and refluxed by heating at 140° C. The reaction solution was stirred for 3 hours and returned to room temperature. The solvent was evaporated under reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=80:1→50:1→5:1) to obtain 135 mg (22%) of orange crystals.

Workup

temperaturerefluxed
customreturned to room temperature
customThe solvent was evaporated under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=80:1→50:1→5:1)

Sources & evidence

ORD record: ord-a13087744c5b49ab9ccb76c4e5f26837
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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