Pyridine → N-(2,4-difluorophenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide

HRID 880060Notes

Reaction equation

HRID 880060 reaction equation
N1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC.[F:19][C:20]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:21]=1[NH2:22].[N:28]1([C:34]2[N:35]=[C:36]([CH2:41][C:42]([O-])=[O:43])[NH:37][C:38](=[O:40])[CH:39]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[Na+]>CN(C)C=O>[F:19][C:20]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:21]=1[NH:22][C:42](=[O:43])[CH2:41][C:36]1[NH:37][C:38](=[O:40])[CH:39]=[C:34]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[N:35]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 97092,4-DifluoroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136041850N-(2,4-difluorophenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamideYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 ml of pyridine, 233 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 400 mg of 2,4-difluoroaniline are added to a solution of 260 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 2 of Example 1 in 2 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 16 hours, and then concentrated under reduced pressure. Water and ethyl acetate are added and the resulting mixture is thus stirred for 30 minutes. The precipitate formed is filtered off, and rinsed with water, ethyl ether and petroleum ether. The solid obtained is dried under vacuum. 205 mg of N-(2,4-difluorophenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained in the form of a pinkish solid, the characteristics of which are the following:

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater and ethyl acetate are added
  3. stirringthe resulting mixture is thus stirred for 30 minutes
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washrinsed with water, ethyl ether and petroleum ether
  7. customThe solid obtained
  8. customis dried under vacuum

Sources & evidence

ORD record
ord-b7af1d964911406086a760a055684f10
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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