Pyridine → N-(3-chloro-4-fluorophenyl)-2-[1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide

HRID 880123Notes

Reaction equation

HRID 880123 reaction equation
N1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[F:27])[NH2:23].[CH3:28][N:29]1[C:34](=[O:35])[CH:33]=[C:32]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[N:31]=[C:30]1[CH2:42][C:43]([O-])=[O:44].[Na+]>CN(C)C=O>[Cl:19][C:20]1[CH:21]=[C:22]([NH:23][C:43](=[O:44])[CH2:42][C:30]2[N:29]([CH3:28])[C:34](=[O:35])[CH:33]=[C:32]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[N:31]=2)[CH:24]=[CH:25][C:26]=1[F:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 97083-Chloro-4-fluoroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57523684Sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate

Product 1

HCID 66553214N-(3-chloro-4-fluorophenyl)-2-[1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamideYield 27.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

120 ml of pyridine, 182 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 210 mg of 3-chloro-4-fluoroaniline are added to a solution of 200 mg of sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate in 2.5 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature overnight and is then concentrated under reduced pressure. Water is added, followed by extraction with ethyl acetate, further washing with water, and concentration under reduced pressure. The residue obtained is washed with ethyl acetate and then rinsed with ethyl ether. 76 mg of N-(3-chloro-4-fluorophenyl)-2-[1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained in the form of a violet solid, the characteristics of which are the following:

Workup

  1. concentrationis then concentrated under reduced pressure
  2. additionWater is added
  3. extractionfollowed by extraction with ethyl acetate
  4. washfurther washing with water, and concentration under reduced pressure
  5. customThe residue obtained
  6. washis washed with ethyl acetate
  7. washrinsed with ethyl ether

Sources & evidence

ORD record
ord-6b36852126764cd69485f111b5e556db
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

Loading…