Hydrochloric Acid → Methyl 2-(isopropylamino)pyrimidine-5-carboxylate

HRID 862708

Reaction equation

HRID 862708 reaction equation
S(O)(O)(=O)=O.[CH:6]([NH:9][C:10]([NH2:12])=[NH:11])([CH3:8])[CH3:7].N1C[CH2:16][CH2:15][CH2:14]1.[CH3:18][O:19]C(C=O)C=O.Cl.[CH3:26][OH:27]>C(OCC)(=O)C>[CH:6]([NH:9][C:10]1[N:12]=[CH:16][C:15]([C:26]([O:19][CH3:18])=[O:27])=[CH:14][N:11]=1)([CH3:8])[CH3:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 31268PyrrolidineHCID 21301831MethoxymalonaldehydeHCID 178457611HCID 178457611, compound

Product 1

HCID 19698832Methyl 2-(isopropylamino)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 11.62 g (77.5 mmol) of isopropyl-guanidine hydrogen sulfate, 32 ml (5 eq; 0.37 mol) of freshly distilled pyrrolidine in 230 ml of anhydrous methanol is refluxed for twenty minutes. A methanolic solution (60 ml) of methoxymalonaldehyde (1 eq; 77.5 mmol; 10 g) is added to the above solution at 0° C. as well as 140 g of molecular sieve (4 A°). The reaction medium is stirred under argon and under reflux for 24 hours. The molecular sieves are removed by filtration and then rinsed with methanol. Evaporation of the filtrate gives a residue which is taken up with ethyl acetate and then acidified with a 1N hydrochloric acid solution. The organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, evaporated and purified on silica gel under 200 mb (eluent: 50 ethyl acetate/50 heptane).

Workup

  1. temperatureis refluxed for twenty minutes
  2. temperatureunder reflux for 24 hours
  3. customThe molecular sieves are removed by filtration
  4. washrinsed with methanol
  5. customEvaporation of the filtrate
  6. customgives a residue which
  7. washThe organic phases are washed with a saturated sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. custompurified on silica gel under 200 mb (eluent: 50 ethyl acetate/50 heptane)

Sources & evidence

ORD record
ord-0dbe75873de14105aca8d34962da0e3b
Source dataset
uspto-grants-1998_02
Patent number
US05719187

Linked notes

Loading…