Benzene → 2,4-Pyrimidinediamine, 6-chloro-N(sup 4)-(2-(diethylamino)ethyl)-N(sup 2),N(sup 2)-dimethyl-5-(methylthio)-

HRID 917939Notes

Reaction equation

HRID 917939 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[N:8]=[C:7]([Cl:9])[C:6]([S:10][CH3:11])=[C:5](Cl)[N:4]=1.C1C=CC=CC=1.[CH2:20]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][NH2:25])[CH3:21]>C(N(CC)CC)C>[CH3:21][CH2:20][N:22]([CH2:23][CH2:24][NH:25][C:5]1[N:4]=[C:3]([N:2]([CH3:1])[CH3:13])[N:8]=[C:7]([Cl:9])[C:6]=1[S:10][CH3:11])[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 241BenzeneHCID 60993N,N-DiethylethylenediamineHCID 15567751HCID 15567751, compound

Product 1

HCID 30433482,4-Pyrimidinediamine, 6-chloro-N(sup 4)-(2-(diethylamino)ethyl)-N(sup 2),N(sup 2)-dimethyl-5-(methylthio)-

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

23.8 parts of 2-dimethylamino-4,6-dichloro-5-methylthio-pyrimidine are placed in 300 parts by volume of benzene and a solution of 12.2 parts of N,N-diethylethylenediamine and 16 parts of triethylamine is added. The mixture is heated under reflux for three hours. After filtering off the triethylamine hydrochloride, the mixture is concentrated, extracted with ether/water, and the organic phase is concentrated and recrystallised from ethyl alcohol. 2-dimethylamino-4-(2'-diethylamine)ethylamino-5-methylthio-6-chloropyrimidine having a melting point of 56°C. is obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for three hours
  3. filtrationAfter filtering off the triethylamine hydrochloride
  4. concentrationthe mixture is concentrated
  5. extractionextracted with ether/water
  6. concentrationthe organic phase is concentrated
  7. customrecrystallised from ethyl alcohol

Sources & evidence

ORD record
ord-24b5c5bbf46742f2bfef854f16bbca0f
Source dataset
uspto-grants-1976_07
Patent number
US03968214

Reaction notes

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