Water → 7-Chloro-2-(chloromethyl)-5-methylsulfanyl-imidazo[1,2-c]pyrimidine

HRID 2389749Notes

Reaction equation

HRID 2389749 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:11][CH2:12][C:13]([CH2:15]Cl)=O.O>C(O)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]2[CH:15]=[C:13]([CH2:12][Cl:11])[N:10]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 107931,3-DichloroacetoneHCID 704964-Amino-6-chloro-2-methylthiopyrimidine

Product 1

HCID 592992327-Chloro-2-(chloromethyl)-5-methylsulfanyl-imidazo[1,2-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

8 g (45.5 mmol) of 6-chloro-2-(methylthio)pyrimidine-4-amine and 5.78 g (45.55 mmol) of 1,3-dichloroacetone are dissolved in 53 ml of glacial acetic acid and heated at 105° C. for 16 h. After the reaction is complete, water is added and the precipitate is filtered off with suction. The crude product is further purified by silica gel chromatography. Drying under high vacuum results in 5.53 g (49% of theory) of product.

Workup

  1. filtrationthe precipitate is filtered off with suction
  2. customThe crude product is further purified by silica gel chromatography
  3. customDrying under high vacuum
  4. customresults in 5.53 g (49% of theory) of product

Sources & evidence

ORD record
ord-810f7b9fa9994d318666bd5bf3c586fb
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

Loading…