Hydrochloric Acid → 6-chloro-N-(2-(methylsulfonyl)ethyl)-2-(4-nitrophenyl)pyrimidin-4-amine

HRID 75456Notes

Reaction equation

HRID 75456 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[N:3]=1.[CH3:18][S:19]([CH2:22][CH2:23][NH2:24])(=[O:21])=[O:20].Cl.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[N:3]=[C:2]([NH:24][CH2:23][CH2:22][S:19]([CH3:18])(=[O:21])=[O:20])[CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 43405612-(Methylsulfonyl)ethanamineHCID 534400054,6-Dichloro-2-(4-nitrophenyl)pyrimidine

Product 1

HCID 866659056-chloro-N-(2-(methylsulfonyl)ethyl)-2-(4-nitrophenyl)pyrimidin-4-amineYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 250 mL round-bottom flask was placed 4,6-dichloro-2-(4-nitrophenyl)pyrimidine (59, 500 mg, 1.85 mmol) in dichloromethane (20 mL) to give a colorless solution. 2-(methylsulfonyl)ethanamine.HCl (325 mg, 2.04 mmol) was added followed by addition of triethylamine (0.77 mL, 5.55 mmol). The mixture was stirred at room temperature for 19 hours and was then refluxed for 21 hour. Excess potassium carbonate was added and heating under reflux was continued for 6 hours. The mixture was cooled to room temperature and stirred at room temperature for 2 weeks. The mixture was diluted with dichloromethane and washed with saturated NaHCO3. The organic phase was dried (MgSO4), filtered and concentrated. The crude product was purified by column chromatography (20-100% ethyl acetate in hexanes) to give the title compound as a yellow solid (196 mg, 30%). HRMS: 357.0417 [M+H]+. For [M+H]+ mass error=−0.2 mDa or −0.60 ppm.

Workup

  1. customIn a 250 mL round-bottom flask was placed
  2. temperaturewas then refluxed for 21 hour
  3. temperatureheating
  4. temperatureunder reflux
  5. waitwas continued for 6 hours
  6. temperatureThe mixture was cooled to room temperature
  7. stirringstirred at room temperature for 2 weeks
  8. washwashed with saturated NaHCO3
  9. dry with materialThe organic phase was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was purified by column chromatography (20-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c52bb2560a704224ab48fb83a2a7fdb5
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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