1,3-Dichloroacetone → 2-(Chloromethyl)-7-(2,4-dichlorophenyl)-5-(ethylsulphanyl)imidazo[1,2-c]pyrimidine

HRID 2171518Notes

Reaction equation

HRID 2171518 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([S:15][CH2:16][CH3:17])[N:12]=[C:11]([NH2:18])[CH:10]=1.[Cl:19][CH2:20][C:21](=O)[CH2:22]Cl>C(O)C>[Cl:19][CH2:20][C:21]1[N:18]=[C:11]2[CH:10]=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[N:14]=[C:13]([S:15][CH2:16][CH3:17])[N:12]2[CH:22]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 583060056-(2,4-Dichlorophenyl)-2-(ethylthio)pyrimidine-4-amine

Product 1

HCID 593129982-(Chloromethyl)-7-(2,4-dichlorophenyl)-5-(ethylsulphanyl)imidazo[1,2-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3 g (9.99 mmol) of 6-(2,4-dichlorophenyl)-2-(ethylsulphanyl)pyrimidine-4-amine (Example 3A) are added to a solution of 1.395 g (10.99 mmol) of 1,3-dichloropropan-2-one in 33 ml of dry ethanol, and the mixture is then heated under reflux conditions for 20 h. The solvent is substantially removed and the residue is purified by preparative HPLC. 1.5 g (37% of theory) of the product are obtained.

Workup

  1. temperaturethe mixture is then heated under reflux conditions for 20 h
  2. customThe solvent is substantially removed
  3. customthe residue is purified by preparative HPLC
  4. custom1.5 g (37% of theory) of the product are obtained

Sources & evidence

ORD record
ord-95e7b41c14b543f681bc1c982b0deb6b
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

Loading…