Water → HCID 19969506, compound

HRID 974817Notes

Reaction equation

HRID 974817 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:17][CH:18]=1)([O-:12])=[O:11].C(=O)([O-])[O-].[Na+].[Na+].O>S1(=O)(=O)CCCC1>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:22]2[CH2:23][CH2:24][N:19]([C:16]3[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:18][N:17]=3)[CH2:20][CH2:21]2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 5889352-Chloro-4-methoxypyrimidineHCID 29287991-(5-Nitropyridin-2-yl)piperazine

Product 1

HCID 19969506HCID 19969506, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-chloro-4-methoxypyrimidine (29 g) and 1-(5-nitro-2-pyridinyl)piperazine (35 g) in tetrahydrothiophene 1,1-dioxide (50 ml) was stirred at 130° C. for 1 hour. The mixture was poured into sodium carbonate and water, stirred for 30 minutes and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered and evaporated. The residue was triturated in diisopropyl ether, yielding 23 g (43%) of 4-methoxy-2-[4-(5-nitro-2-pyridinyl)-1-piperazinyl]pyrimidine (interm. 10).

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-599da87ba36f4ac498abaa3e0d6f7f43
Source dataset
uspto-grants-1997_03
Patent number
US05607932

Reaction notes

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