Dimethylamine → 6-chloro-N,N-dimethyl-5-nitropyrimidin-4-amine

HRID 1451041Notes

Reaction equation

HRID 1451041 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[CH3:12][NH:13][CH3:14].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:12][N:13]([CH3:14])[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 203124,6-Dichloro-5-nitropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 71136226-chloro-N,N-dimethyl-5-nitropyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

Dissolve 50 g (0.26 mol) of 4,6-dichloro-5-nitropyrimidine in 500 mL of CH2Cl2 and cool to -70° C. Add a solution of 24 mL (0.28 mol) dimethylamine, 70 mL (0.40 mol) of diisopropylethylamine, and 100 mL of CH2Cl2 over 30 minutes. Warm to room temperature and wash the reaction mixture with 500 mL of 20% K2CO3. Dry the CH2Cl2 portion over MgSO4, treat with charcoal filter, and remove the filtrate under vacuum. Crystallize the residue with ether to provide 4-dimethylamino-6-chloro-5-nitropyrimidine.

Workup

  1. temperatureWarm to room temperature
  2. washwash the reaction mixture with 500 mL of 20% K2CO3
  3. dry with materialDry the CH2Cl2 portion over MgSO4
  4. additiontreat with charcoal
  5. filtrationfilter
  6. customremove the filtrate under vacuum
  7. customCrystallize the residue with ether

Sources & evidence

ORD record
ord-1887ab2d571c40ad9f712b9cc9024bf4
Source dataset
uspto-grants-1997_02
Patent number
US05602252

Reaction notes

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