1,4-Dioxane → 7-(2,4-Dichlorophenyl)-5-(ethylthio)imidazo[1,2-c]pyrimidine

HRID 2171474Notes

Reaction equation

HRID 2171474 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.CO[CH:21](OC)[CH2:22]Br.O1CCOCC1>O>[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]2[CH:21]=[CH:22][N:18]=[C:11]2[CH:10]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 816722-Bromo-1,1-dimethoxyethaneHCID 583060056-(2,4-Dichlorophenyl)-2-(ethylthio)pyrimidine-4-amine

Product 1

HCID 593131257-(2,4-Dichlorophenyl)-5-(ethylthio)imidazo[1,2-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

48.5 g (161.55 mmol) of 6-(2,4-dichlorophenyl)-2-(ethylthio)pyrimidine-4-amine (Example 3A) and 163.84 g (969.32 mmol) of bromoacetaldehyde dimethyl acetal are introduced into a mixture of 1164 ml of dioxane and 291 ml of water and heated under reflux for 16 h. The dioxane is substantially removed in vacuo, and 1000 ml of ethyl acetate and 1000 ml of saturated aqueous sodium bicarbonate solution are cautiously added. The phases are separated and a further extraction with ethyl acetate is carried out. The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and then freed of solvent. The residue is purified by silica gel chromatography. 16.6 g (27% of theory) of the product are obtained and are reacted further in this form.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 h
  3. customThe dioxane is substantially removed in vacuo, and 1000 ml of ethyl acetate and 1000 ml of saturated aqueous sodium bicarbonate solution
  4. additionare cautiously added
  5. customThe phases are separated
  6. extractiona further extraction with ethyl acetate
  7. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. customThe residue is purified by silica gel chromatography
  10. custom16.6 g (27% of theory) of the product are obtained
  11. customare reacted further in this form

Sources & evidence

ORD record
ord-385f2a3c8caf4b9eb9fa994765381ca2
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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