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

HRID 1723677Notes

Reaction equation

HRID 1723677 reaction equation
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9](Cl)[N:8]=[CH:7][N:6]=1>CO>[Cl:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:2][CH3:1])[N:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 203124,6-Dichloro-5-nitropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 2522044-chloro-6-methoxy-5-nitropyrimidineYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium methoxide (2.70 g, 50.0 mmol) was added portionwise over 10 min to a 0° C. suspension of 4,6-dichloro-5-nitropyrimidine (4.85 g, 25.0 mmol) in methanol (90 ml). On complete addition the mixture was stirred at 0° C for 2 h. The precipitate was filtered and the filtrate evaporated. The residue was suspended in isohexane and filtered. The filtrate was evaporated and the residue purified by flash column chromatography on silica, eluting with 5% ethyl acetate in isohexane. Collecting appropriate fractions gave 4-chloro-6-methoxy-5-nitropyrimidine (3.50 g, 74%) as a white solid: δH (400 MHz, CDCl3) 4.15 (3H, s), 8.65 (1H, s).

Workup

  1. additionOn complete addition the mixture
  2. filtrationThe precipitate was filtered
  3. customthe filtrate evaporated
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue purified by flash column chromatography on silica
  7. washeluting with 5% ethyl acetate in isohexane
  8. customCollecting appropriate fractions

Sources & evidence

ORD record
ord-07e7aec29ab64322bb7090cab3ebf0c3
Source dataset
uspto-grants-2009_02
Patent number
US07485640B2

Reaction notes

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