4,6-Dichloro-5-nitropyrimidine → 4-chloro-6-methoxy-5-nitropyrimidine

HRID 1388892Notes

Reaction equation

HRID 1388892 reaction equation
[N+:1]([C:4]1[C:5]([Cl:11])=[N:6][CH:7]=[N:8][C:9]=1Cl)([O-:3])=[O:2].C[CH2:13][O-:14].[Na+]>>[Cl:11][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[C:9]([O:14][CH3:13])[N:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 203124,6-Dichloro-5-nitropyrimidineHCID 2723922Sodium ethoxide

Product 1

HCID 2522044-chloro-6-methoxy-5-nitropyrimidineYield 98.3%

Procedure

100 g 5-nitro 4,6-dichloropyrimidine are heated in 1000 ml sodium ethylate solution (16.8 g sodium) for 10 hours to 50° C. Then the reaction mixture is evaporated under vacuum and the residue is stirred with water and vacuum treated. Subsequently, it is extracted several times with hot petroleum ether (boiling range 40° to 60° C.). After cooling, the crystals are vacuum treated and dried. 46 g 4-chloro-6-methoxy-5-nitropyrimidine are obtained having a melting point of 65° C.

Workup

  1. customThen the reaction mixture is evaporated under vacuum
  2. additiontreated
  3. extractionSubsequently, it is extracted several times with hot petroleum ether (boiling range 40° to 60° C.)
  4. temperatureAfter cooling
  5. additiontreated
  6. customdried

Sources & evidence

ORD record
ord-a50f6e391acb4900bcd05d226c670c22
Source dataset
uspto-grants-1984_02
Patent number
US04434167

Reaction notes

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