Methylamine → N-Methyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxamide

HRID 486237Notes

Reaction equation

HRID 486237 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])=[N:5][CH:4]=[C:3]1[C:18]([O:20]CC)=O.[CH3:23][NH2:24]>>[CH3:23][NH:24][C:18]([C:3]1[C:2](=[O:1])[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])=[N:5][CH:4]=1)=[O:20]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 12535801Ethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxylate

Product 1

HCID 19097739N-Methyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxamide

Procedure

Ethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxylate (1 g, U.S. Pat. No. 4,031,093) was treated with methylamine (33% in industrial methylated spirit, 50 ml) in a pressure vessel (379 kPa) at 120° C. for six hours and then allowed to cool. Solvent was removed under reduced pressure to afford a white solid which was triturated with ether, 0.88 g, m.p. 190°-191° C. This solid together with another sample prepared similarly (0.32 g) was recrystallised from ethanol to afford the title compound, 0.98 g, m.p. 192°-193° C.

Workup

  1. temperatureto cool
  2. customSolvent was removed under reduced pressure
  3. customto afford a white solid which
  4. customwas triturated with ether, 0.88 g, m.p. 190°-191° C
  5. customThis solid together with another sample prepared similarly (0.32 g)
  6. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-39771296fe9e446d9a539eb2d18d6346
Source dataset
uspto-grants-1994_03
Patent number
US05290933

Reaction notes

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