HCID 3145500, compound → HCID 15392100, compound

HRID 619125Notes

Reaction equation

HRID 619125 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][CH:18]=[CH:17][C:16]=1[CH:21]1[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:25]([CH3:32])[NH:24][C:23](=[S:33])[NH:22]1>O1CCCC1>[Cl:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:5]=1[C:2]1[S:33][C:23]2=[N:24][C:25]([CH3:32])=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][CH3:13])[N:22]2[CH:3]=1

Participants

4

Reactant 2

HCID 3145500HCID 3145500, compoundHCID 11032855HCID 11032855, compound

Product 1

HCID 15392100HCID 15392100, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.0 g (7.5 mmol) of α-bromo-2,6-dichlorophenyl-acetaldehyde and 2.08 g (6.8 mmol) of ethyl (RS)-4-(2-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate in 40 ml of tetrahydrofuran was stirred at RT for 17 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 24 h. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (ethyl acetate). There were obtained 1.82 g (51%) of ethyl (RS)-2-(2,6-dichlorophenyl)-5-(2-methoxyphenyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate 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 24 h
  7. concentrationThe reaction mixture was concentrated
  8. customthe residue was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-9fc451155f804578a059127690f556e1
Source dataset
uspto-grants-1999_09
Patent number
US05958931

Reaction notes

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