4-[(E)-2-(4-Isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-pyridinamine → 2-Hydroxy-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1828487Notes

Reaction equation

HRID 1828487 reaction equation
[CH:1]([C:4]1[N:5]=[C:6](/[CH:9]=[CH: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=CC=CC=1>[OH:23][C:18]1[N:17]=[C:13]2[CH:12]=[C:11](/[CH:10]=[CH: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

4

Reactant 2

HCID 220635144-[(E)-2-(4-Isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-pyridinamine2×HCID 22063717Trichlorophenyl malonate

Product 1

HCID 1363468402-Hydroxy-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4H-pyrido[1,2-a]pyrimidin-4-oneYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 4-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-pyridinamine (2.65 g, 10.8 mmol) obtained in (D) was dissolved in toluene (100 ml), added with trichlorophenyl malonate (5.50 g, 11.9 mmol), and refluxed by heating for 1.5 hours. After the reaction mixture was concentrated, the deposited solid was collected by filtration and washed with n-hexane and ether to obtain the title compound (3.14 g, 93%) as yellow solid.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 1.5 hours
  3. concentrationAfter the reaction mixture was concentrated
  4. filtrationthe deposited solid was collected by filtration
  5. washwashed with n-hexane and ether

Sources & evidence

ORD record
ord-5595721567744e4c9c25b60897275712
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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