Methanol → HCID 13394197, compound

HRID 1285191Notes

Reaction equation

HRID 1285191 reaction equation
[CH3:1][OH:2].[Na].[NH2:4][C:5]1[CH:10]=[C:9](Cl)[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[N:6]=1.O>C(Cl)(Cl)Cl>[NH2:4][C:5]1[CH:10]=[C:9]([O:2][CH3:1])[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[N:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 5360545SodiumHCID 13537839HCID 13537839, compound

Product 1

HCID 13394197HCID 13394197, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 25 ml of methanol and 1.1 g (0.048 mole) of sodium was added 5.1 g (0.030 mole) of 4-amino-6-chloro-2-(n-propyl)pyrimidine, and the resulting mixture was heated at reflux for four days. The mixture was allowed to cool to about 20° C., at which time water and chloroform were added thereto. The layers were separated, and the aqueous layer was extracted with additional chloroform. The organic layers were combined, dried over magnesium sulfate, and evaporated to provide a residue. The residue was recrystallized from cyclohexane with treatment with decolorizing charcoal to provide white solid 4-amino-6-methoxy-2-(n-propyl)pyrimidine, m.p. 97°-99° C. The structural assignment was supported by nuclear magnetic resonance and infrared spectral analyses.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for four days
  3. additionwere added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with additional chloroform
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto provide a residue
  9. customThe residue was recrystallized from cyclohexane with treatment with decolorizing charcoal

Sources & evidence

ORD record
ord-d012b545571e414c814ad89fe199b393
Source dataset
uspto-grants-1986_01
Patent number
US04565864

Reaction notes

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