Ammonia → HCID 16426513, compound

HRID 2206843Notes

Reaction equation

HRID 2206843 reaction equation
[Cl:1][C:2]1[C:3]([C:10](Cl)=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[NH3:13].O>O1CCOCC1.CO>[Cl:1][C:2]1[C:3]([C:10]([NH2:13])=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 140671885-Chloro-2-(methylsulfanyl)pyrimidine-4-carbonyl chloride

Product 1

HCID 16426513HCID 16426513, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
5 °C

Procedure

15 g (67.2 mmol) of 5-chloro-2-(methylsulfanyl)pyrimidine-4-carbonyl chloride are dissolved in 35 ml of dioxane and cooled to 5° C. 57.3 g (0.4 mol) of 7N ammonia in methanol (about 12% strength solution) are slowly added dropwise to the cooled solution. During the addition, the reaction temperature was kept below 15° C. After the dropwise addition had ended, the reaction mixture was allowed to warm to room temperature and stirred for about 15 hours. The mixture was then added to water and the precipitated 5-chloro-2-(methylsulfanyl)pyrimidine-4-carboxamide was isolated (7.7 g, yield 53% at a purity of 95%).

Workup

  1. additionDuring the addition
  2. customwas kept below 15° C
  3. additionAfter the dropwise addition
  4. temperatureto warm to room temperature

Sources & evidence

ORD record
ord-0c7c34a76b774d5ea75187e804e921d9
Source dataset
uspto-grants-2016_06
Patent number
US09375002B2

Reaction notes

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