Chlorosuccinimide → 4,5-Dichloro-6-phenyl-2-pyrimidinamine

HRID 2291347Notes

Reaction equation

HRID 2291347 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH2:14])[N:3]=1.[Cl:15]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:1][C:2]1[C:7]([Cl:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH2:14])[N:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 2408022-Amino-4-chloro-6-phenylpyrimidine

Product 1

HCID 212799544,5-Dichloro-6-phenyl-2-pyrimidinamineYield 51.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
-20 °C

Procedure

To 1.5 g (7.3 mM) of 4-chloro-6-phenyl-2-pyrimidinamine is added 40 ml of glacial acetic acid and 1.05 g of N-chlorosuccinimide. The reaction is stirred at ambient temperature (-20° C.) for 18 hours. The reaction mixture is evaporated to dryness, dissolved in acetone and 10.0 g of silica gel added and the mixture evaporated to a powder under vacuum. The powder is chromatographed on 50 g silica gel and eluted with 35% ethyl acetate/hexane. A fraction containing material with a TLC r.f. of 0.7 35% ethylacetate/hexane is collected and evaporated to dryness, recrystallized from acetone/Skellysolve B (1:10), evaporated to dryness(?) to yield 0.90 g of 4,5-dichloro-6-phenyl-2-pyrimidinamine.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. dissolutiondissolved in acetone
  3. addition10.0 g of silica gel added
  4. customthe mixture evaporated to a powder under vacuum
  5. customThe powder is chromatographed on 50 g silica gel
  6. washeluted with 35% ethyl acetate/hexane
  7. additionA fraction containing material with a TLC r.f
  8. customof 0.7 35% ethylacetate/hexane is collected
  9. customevaporated to dryness
  10. customrecrystallized from acetone/Skellysolve B (1:10)
  11. customevaporated

Sources & evidence

ORD record
ord-0567fc7779cc4b6aa27e6d57856a73a7
Source dataset
uspto-grants-1989_01
Patent number
US04795812

Reaction notes

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