2-Chlorobenzaldehyde → HCID 67447519, compound

HRID 2370068Notes

Reaction equation

HRID 2370068 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][CH2:10][CH2:11][S:12][CH3:13])[C:3]=1[NH2:14].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH:25]=O>COC1C=CC=CC=1>[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[C:25]1[N:9]([CH2:10][CH2:11][S:12][CH3:13])[C:4]2[C:3]([N:14]=1)=[C:2]([N:19]1[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]1)[N:7]=[C:6]([CH3:8])[N:5]=2

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 531671-MethylpiperazineHCID 86675236HCID 86675236, compound

Product 1

HCID 67447519HCID 67447519, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Dissolve 6-chloro-2-methyl-N4-(2-(methylthio)ethyl)pyrimidine-4,5-diamine (28.1 g, 120.7 mmol), and N-methyl piperazine (14.76 ml, 132.81 mmol) in methoxybenzene in a 2 L round bottom flask. Add 2-chlorobenzaldehyde (20.38 mL, 181.1 mmol) in one portion and raise the temperature to 140° C. and maintain at this temperature for 4 days. Cool the reaction mixture and concentrate under reduced pressure. Dilute the resulting oil with 2 N aqueous hydrogen chloride (200 mL) and wash with dichloromethane (500 mL). Discard the organic layer. Treat the aqueous layer with a sodium hydroxide solution until pH=14 is attained. Extract into dichloromethane. Dry the organics over anhydrous sodium sulfate, filter, and concentrate to give the title compound as a brown oil (43 g). ES/MS m/z 417 (M+1).

Workup

  1. temperaturemaintain at this temperature for 4 days
  2. temperatureCool the reaction mixture
  3. concentrationconcentrate under reduced pressure
  4. additionDilute the resulting oil with 2 N aqueous hydrogen chloride (200 mL)
  5. washwash with dichloromethane (500 mL)
  6. additionTreat the aqueous layer with a sodium hydroxide solution until pH=14
  7. extractionExtract into dichloromethane
  8. dry with materialDry the organics over anhydrous sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-d94beb856a9a4419ab985a01f32cca06
Source dataset
uspto-grants-2014_04
Patent number
US08710063B2

Reaction notes

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