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

HRID 2171479Notes

Reaction equation

HRID 2171479 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-59416aa5f5b547bab0f7a134fa85eb0e
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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