219806-93-6 → HCID 11123147, compound

HRID 619123Notes

Reaction equation

HRID 619123 reaction equation
Br[CH:2]([C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12])[CH:3]=O.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[C:26]([C:27](=[O:29])[CH3:28])=[C:25]([CH3:30])[NH:24][C:23](=[S:31])[NH:22]2)=[CH:17][CH:16]=1>O1CCCC1>[Cl:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:5]=1[C:2]1[S:31][C:23]2=[N:24][C:25]([CH3:30])=[C:26]([C:27](=[O:29])[CH3:28])[CH:21]([C:18]3[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=3)[N:22]2[CH:3]=1

Participants

4

Reactant 2

HCID 3097577219806-93-6HCID 11032855HCID 11032855, compound

Product 1

HCID 11123147HCID 11123147, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.9 g (7.09 mmol) of α-bromo-2,6-dichlorophenyl-acetaldehyde and 1.78 g (6.45 mmol) of (RS)-1-[4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]ethanone in 50 ml of tetra- hydrofuran was stirred at RT for 65 h. Subsequently, the mixture was cooled to 0° C. and the precipitated solid was filtered off, dissolved in 75 ml of conc. acetic acid and heated at reflux while stirring for 8 h. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (dichloromethane/methanol 95:5). There were obtained 1.95 g (68%) of (RS)-1-[2-(2,6-dichlorophenyl)-5-(4-methoxyphenyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-6-yl]ethanone as a yellow foam.

Workup

  1. temperatureSubsequently, the mixture was cooled to 0° C.
  2. filtrationthe precipitated solid was filtered off
  3. dissolutiondissolved in 75 ml of conc. acetic acid
  4. temperatureheated
  5. temperatureat reflux
  6. stirringwhile stirring for 8 h
  7. concentrationThe reaction mixture was concentrated
  8. customthe residue was purified by column chromatography on silica gel (dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-5859713c8c874eb0a9f526e907716d9e
Source dataset
uspto-grants-1999_09
Patent number
US05958931

Reaction notes

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