Chloroacetaldehyde → 7-Chloro-5-(methylthio)imidazo[1,2-c]pyrimidine hydrochloride

HRID 1852952Notes

Reaction equation

HRID 1852952 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH2:10])[CH:3]=1.Cl[CH2:12][CH:13]=O>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]2[CH:12]=[CH:13][N:10]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 704964-Amino-6-chloro-2-methylthiopyrimidine

Product 1

HCID 866852967-Chloro-5-(methylthio)imidazo[1,2-c]pyrimidine hydrochlorideYield 141.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-chloro-2-(methylthio)pyrimidin-4-amine (25.17 g, 143.3 mmol) and 2-chloroacetaldehyde (27.73 mL, 215.0 mmol) (50% aqueous) in 1,4-dioxane (50 mL) was heated at 95° C. for 14 hours. The reaction mixture was allowed to cool to ambient temperature and then cooled in an ice bath. The reaction mixture was filtered and the solids washed with dioxane to afford 7-chloro-5-(methylthio)imidazo[1,2-c]pyrimidine hydrochloride (24.01 g, 101.7 mmol, 70.96% yield) as a tan powder. MS (apci) m/z=200.0 (M+H).

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe reaction mixture was filtered
  3. washthe solids washed with dioxane

Sources & evidence

ORD record
ord-251e096ea02f45c4b971baeb60146df3
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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