4-Amino-6-chloro-2-methylthiopyrimidine → 7-Chloro-5-(methylthio)imidazo[1,2-c]pyrimidine

HRID 2389740Notes

Reaction equation

HRID 2389740 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.CO[CH:13](OC)[CH2:14]Br>O1CCOCC1.O>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]2[CH:13]=[CH:14][N:1]=[C:2]2[CH:7]=1

Participants

5

Reactant 2

HCID 704964-Amino-6-chloro-2-methylthiopyrimidineHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 408159747-Chloro-5-(methylthio)imidazo[1,2-c]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

75 g (427 mmol) of 4-amino-6-chloro-2-(methylthio)pyrimidine are dissolved in 3000 ml of dioxane and 750 ml of water. 101.05 g (597.81 mmol) of bromoacetaldehyde dimethyl acetal are added, and the mixture is heated under reflux for 24 h. After the reaction is complete, the dioxane is removed in vacuo and the aqueous suspension is suspended in THF, filtered with suction and washed with some THF. Drying of the solid at 40° C. under high vacuum results in 56.5 g (66% of theory) of the product.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 24 h
  3. customthe dioxane is removed in vacuo
  4. filtrationfiltered with suction
  5. washwashed with some THF
  6. customDrying of the solid at 40° C. under high vacuum
  7. customresults in 56.5 g (66% of theory) of the product

Sources & evidence

ORD record
ord-dfde25595bbb489080078c5b97d2e8d4
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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