Sodium Hydroxide → N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro4-pyridyl)-2-pyrimidineamine

HRID 724826Notes

Reaction equation

HRID 724826 reaction equation
[N+]([O-])(O)=O.[CH2:5]([O:7][C:8]([C:10]1[CH:11]=[C:12]([NH:16][C:17]([NH2:19])=[NH:18])[CH:13]=[CH:14][CH:15]=1)=[O:9])[CH3:6].CN(C)[CH:22]=[CH:23][C:24]([C:26]1[CH:31]=[CH:30][N:29]=[C:28]([Cl:32])[CH:27]=1)=O.[OH-].[Na+]>C(O)C(C)C>[CH2:5]([O:7][C:8]([C:10]1[CH:11]=[C:12]([NH:16][C:17]2[N:19]=[C:24]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([Cl:32])[CH:27]=3)[CH:23]=[CH:22][N:18]=2)[CH:13]=[CH:14][CH:15]=1)=[O:9])[CH3:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 544350393-Dimethylamino-1-(2-chloro4-pyridyl)-2-propen-1-oneHCID 178468910HCID 178468910, compound

Product 1

HCID 19689549N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro4-pyridyl)-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

14.5 g (53.7 mmol) of 3-ethoxycarbonyl-phenyl-guanidine nitrate, 11.3 g (53.7 mmol) of 3-dimethylamino-1-(2-chloro4-pyridyl)-2-propen-1-one and 2.4 g (60 mmol) of sodium hydroxide are stirred in 150 ml of isobutanol for 14 hours at 110°. After cooling, washing twice with 100 ml of ethanol each time and crystallising (tetra-hydrofuran/ethanol), N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro4-pyridyl)-2-pyrimidineamine is obtained; m.p. 149°-150°, FAB-MS: 355 (M+ +H).

Workup

  1. temperatureAfter cooling
  2. washwashing twice with 100 ml of ethanol each time
  3. customcrystallising (tetra-hydrofuran/ethanol)

Sources & evidence

ORD record
ord-350217ff633a4adb92efcce968455ad8
Source dataset
uspto-grants-1998_01
Patent number
US05705502

Reaction notes

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