Pyridine → N-[3-(dimethylamino)phenyl]-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide

HRID 1631552Notes

Reaction equation

HRID 1631552 reaction equation
N1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC.[CH3:19][N:20]([CH3:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=1.[N:29]1([C:35]2[N:36]=[C:37]([CH2:42][C:43]([O-])=[O:44])[NH:38][C:39](=[O:41])[CH:40]=2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[Na+]>CN(C)C=O.ClCCl.C(OCC)C.CO>[CH3:19][N:20]([CH3:28])[C:21]1[CH:22]=[C:23]([NH:27][C:43](=[O:44])[CH2:42][C:37]2[NH:38][C:39](=[O:41])[CH:40]=[C:35]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:36]=2)[CH:24]=[CH:25][CH:26]=1

Participants

9

Reactant 4

HCID 1049PyridineHCID 76084N,N-dimethyl-m-phenylenediamineHCID 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 136041849N-[3-(dimethylamino)phenyl]-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamideYield 8.8%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

0.160 ml of pyridine, 240 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 400 mg of N,N-dimethyl-m-phenylenediamine are added to a solution of 250 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 2 of Example 1 in 4 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature overnight and is 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, rinsed with ethyl ether and dried in a rotary evaporator. After purification by silica column chromatography as a solid deposit, eluent: dichloromethane/methanol 95/05, a solid is obtained which is taken up in a mixture of dichloromethane, methanol and ethyl ether. The solid is filtered off and dried. 30 mg of N-[3-(dimethylamino)phenyl]-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained in the form of a yellow solid, the characteristics of which are the following:

Workup

  1. concentrationis then concentrated 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 ethyl ether
  7. customdried in a rotary evaporator
  8. customAfter purification by silica column chromatography as a solid deposit, eluent
  9. customdichloromethane/methanol 95/05, a solid is obtained which
  10. filtrationThe solid is filtered off
  11. customdried

Sources & evidence

ORD record
ord-6b98542af6b0495494d77c25d9689bb4
Source dataset
uspto-grants-2014_07
Patent number
US08791255B2

Reaction notes

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