Sodium Carbonate → 4-(Methoxymethyl)-6-methyl-N-phenylpyrimidin-2-amine

HRID 981481Notes

Reaction equation

HRID 981481 reaction equation
[N+]([O-])(O)=O.[C:5]1([NH:11][C:12]([NH2:14])=[NH:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:15][O:16][CH2:17][C:18]([CH2:20][C:21](=O)[CH3:22])=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[NH:11]([C:12]1[N:14]=[C:18]([CH2:17][O:16][CH3:15])[CH:20]=[C:21]([CH3:22])[N:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2217341-Methoxy-2,4-pentanedioneHCID 178418691HCID 178418691, compound

Product 1

HCID 143275464-(Methoxymethyl)-6-methyl-N-phenylpyrimidin-2-amineYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.5 g of phenylguanidine nitrate, 3.3 g of methoxyacetylacetone and 12 g of anhydrous sodium carbonate was heated with stirring and allowed to react at 150° C. for 2 hours. After cooling to room temperature, water was added to the reaction mixture, which was then extracted with 150 ml of toluene. The toluene layer was washed with water, dried over Glauber's salt and concentrated by evaporation under reduced pressure. The residue was purified by silica gel column chromatography to obtain 3.5 g (yield: 68%) of 2-anilino-4-methoxymethyl-6-methylpyrimidine.

Workup

  1. temperaturewas heated
  2. customto react at 150° C. for 2 hours
  3. extractionwas then extracted with 150 ml of toluene
  4. washThe toluene layer was washed with water
  5. dry with materialdried over Glauber's salt
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7944efe6baa448f8a4b0c8c02cee3a12
Source dataset
uspto-grants-1991_02
Patent number
US04992438

Reaction notes

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