Isopropanol → N-{4-Chloro-5-[(4-chlorophenyl)ethynyl]pyrimidin-2-yl}formamide

HRID 1271043Notes

Reaction equation

HRID 1271043 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:6][N:5]=[C:4]([N:17]=[CH:18]N(C)C)[N:3]=1.C([OH:25])(C)C.CS(O)(=O)=O>O>[Cl:1][C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:6][N:5]=[C:4]([NH:17][CH:18]=[O:25])[N:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6395Methanesulfonic AcidHCID 73446453HCID 73446453, compound

Product 1

HCID 18452568N-{4-Chloro-5-[(4-chlorophenyl)ethynyl]pyrimidin-2-yl}formamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-5-(4-chlorophenylethynyl)-2-dimethylaminomethyleneaminopyrimidine (65.1 g), isopropanol (585 mL), and water (36 mL) were combined and warmed to 60° C. Methane sulfonic acid (23.1 g) was added and heating at 60oC was continued for 1.5–2.0 hours or until HPLC analysis confirmed the absence of the starting material. The mixture was cooled to ambient temperature and held for 1.5 hours. The solids were removed by filtration and washed with isopropanol (100 mL). The filter cake was slurried in water (500 mL), basified with 1 N NaOH to pH 11, filtered, and the solids were rinsed with water. Vacuum drying at 50° C. provided predominantly 4-chloro-5-(4-chlorophenylethynyl)-2-formamidopyrimidine: 51.6 g.

Workup

  1. temperatureheating at 60oC
  2. waitwas continued for 1.5–2.0 hours or until HPLC analysis
  3. temperatureThe mixture was cooled to ambient temperature
  4. customThe solids were removed by filtration
  5. washwashed with isopropanol (100 mL)
  6. filtrationfiltered
  7. washthe solids were rinsed with water
  8. customVacuum drying at 50° C.

Sources & evidence

ORD record
ord-d5877f3b71854fe0901f0cbad4d0df7a
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Reaction notes

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