2-Aminopyrimidine → 5-(3-Methylimidazo-[1,2-a]pyrimidin-2-yl)-2-benzothiazolinone

HRID 1731336Notes

Reaction equation

HRID 1731336 reaction equation
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11](=[O:13])[NH:10][C:9]=2[CH:14]=1)=O.[NH2:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1>C(#N)C>[CH3:15][C:2]1[N:18]2[CH:19]=[CH:20][CH:21]=[N:22][C:17]2=[N:16][C:3]=1[C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11](=[O:13])[NH:10][C:9]=2[CH:14]=1

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 202287105-(2-Bromopropanoyl)-1,3-benzothiazol-2(3H)-one

Product 1

HCID 202287255-(3-Methylimidazo-[1,2-a]pyrimidin-2-yl)-2-benzothiazolinoneYield 50.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(2-bromopropionyl)-2-benzothiazolinone (2.9 g) and 2-aminopyrimidine (2.9 g) in acetonitrile (100 ml) was refluxed for 15 hours with stirring. The reaction mixture was cooled to ambient temperature to give a precipitate, which was collected by filtration. The precipitate was added to a mixture of water and ethyl acetate and the resulting mixture was adjusted to pH 8.0 with 20% aqueous potassium carbonate solution. The precipitate was collected by filtration, washed successively with water and ethanol and dried over phosphorus pentoxide to give 5-(3-methylimidazo-[1,2-a]pyrimidin-2-yl)-2-benzothiazolinone (1.45 g).

Workup

  1. customto give a precipitate, which
  2. filtrationwas collected by filtration
  3. additionThe precipitate was added to a mixture of water and ethyl acetate
  4. filtrationThe precipitate was collected by filtration
  5. washwashed successively with water and ethanol
  6. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-31cd670681d1475ab497bd781724d8ff
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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