Pyridine → HCID 136041830, compound

HRID 880195Notes

Reaction equation

HRID 880195 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:9]=1.[N:20]1([C:26]2[N:27]=[C:28]([CH2:33][C:34]([O-])=[O:35])[NH:29][C:30](=[O:32])[CH:31]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.[Na+]>CN(C)C=O>[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:34](=[O:35])[CH2:33][C:28]2[NH:29][C:30](=[O:32])[CH:31]=[C:26]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:27]=2)=[C:10]([O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 18069889HCID 18069889, compoundHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136041830HCID 136041830, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 ml of pyridine, 500 mg of N-[3-(dimethylamino)propyl]-N-ethylcarbodiimide hydrochloride and 590 mg of 4-fluoro-2-(2-methoxyethoxy)phenylamine are added to a solution of 500 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 2 of example 1, in 3 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 15 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. 155 mg of N-[4-fluoro-2-(2-methoxyethoxy)phenyl]-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-c6d8a14518ea40f592863670e19eb832
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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