Sodium Methoxide → 2-Methoxy-4-sec. butylamino-5nitro-6-methylpyrimidine

HRID 597466Notes

Reaction equation

HRID 597466 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:11][CH3:12])[CH3:10])[C:5]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:16])[N:3]=1.[CH3:17][O-:18].[Na+]>CO>[CH3:17][O:18][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:11][CH3:12])[CH3:10])[C:5]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:16])[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18801449HCID 18801449, compound

Product 1

HCID 214450672-Methoxy-4-sec. butylamino-5nitro-6-methylpyrimidineYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

17.1 g of 2-chloro-4-sec. butylamino-5-nitro-6-methyl-pyrimidine (0.07 mole) are dissolved in 200 ml of methanol. To this solution is added a solution of 8.1 g of sodium methylate (0.15 mole) in 100 ml of methanol and the mixture is boiled overnight at 100° C bath temperature. After it has been cooled, the solution is evaporated and the resultant red substance is treated with ether and then filtered over Hyflo. The filter residue is washed 5 times with ether and the combined ethereal extracts are then evaporated to yield 12.3 g of 2-methoxy-4-sec. butylamino-5nitro-6-methylpyrimidine which boils at 110° C at 0.001 Torr (=73% yield).

Workup

  1. temperatureAfter it has been cooled
  2. customthe solution is evaporated
  3. additionthe resultant red substance is treated with ether
  4. filtrationfiltered over Hyflo
  5. washThe filter residue is washed 5 times with ether
  6. customthe combined ethereal extracts are then evaporated

Sources & evidence

ORD record
ord-dccb631b73f543d3b8d59a1c7c4dbf68
Source dataset
uspto-grants-1977_03
Patent number
US04014677

Reaction notes

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