Ethanol → Ethyl 6-amino-5-chloro-2-(4-chlorophenyl)pyrimidine-4-carboxylate

HRID 249664

Reaction equation

HRID 249664 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]([OH:17])=[O:16])[C:3]=1[Cl:18].S(Cl)(Cl)=O.O.[OH-].[Na+].[CH2:26](O)[CH3:27]>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]([O:17][CH2:26][CH3:27])=[O:16])[C:3]=1[Cl:18]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 468639846-Amino-5-chloro-2-(4-chlorophenyl)pyrimidine-4-carboxylic acid

Product 1

HCID 46863983Ethyl 6-amino-5-chloro-2-(4-chlorophenyl)pyrimidine-4-carboxylate

Procedure

To a solution of 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid (i.e. the product of Example 4, Step C) (20.0 g, 70.4 mmol) in ethanol (70 mL) was added thionyl chloride (5.14 mL, 70.4 mmol) while maintaining the temperature below 15° C. using an ice bath. The reaction mixture was then heated at reflux overnight. Water was added. Then with external cooling aqueous sodium hydroxide (50%) was added to adjust the pH to 7. The resulting solid was isolated by filtration and dried to afford the title product, a compound of the present invention, as a light beige solid (20.1 g).

Workup

  1. temperaturewhile maintaining the temperature below 15° C.
  2. temperatureThe reaction mixture was then heated
  3. temperatureat reflux overnight
  4. customThe resulting solid was isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-f2b7e6e92b6e4f0fa5502f30bcca4b8a
Source dataset
uspto-grants-2011_01
Patent number
US07863220B2

Linked notes

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