Aniline → 2-[4-(Morpholin-4-Yl)-6-Oxo-1,6-Dihydropyrimidin-2-Yl]-N-Phenylacetamide

HRID 880057Notes

Reaction equation

HRID 880057 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.ON1C2C=CC=CC=2N=N1.NC1C=CC=CC=1.[N:45]1([C:51]2[N:52]=[C:53]([CH2:58][C:59]([O-])=[O:60])[NH:54][C:55](=[O:57])[CH:56]=2)[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1.[Na+]>CN(C)C=O>[N:45]1([C:51]2[N:52]=[C:53]([CH2:58][C:59]([NH:8][C:12]3[CH:11]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:60])[NH:54][C:55](=[O:57])[CH:56]=2)[CH2:46][CH2:47][O:48][CH2:49][CH2:50]1

Participants

6

Reactant 4

HCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 1355667412-[4-(Morpholin-4-Yl)-6-Oxo-1,6-Dihydropyrimidin-2-Yl]-N-PhenylacetamideYield 66.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

370 mg of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 113 mg of 1-hydroxybenzotriazole and 0.140 ml of aniline are added to a solution of 200 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 3 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 dried in a rotary evaporator. After purification by silica column chromatography, eluent: dichloromethanemethanol 90/10, 161 mg of 2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]-N-phenylacetamide are obtained in the form of a white 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. customdried in a rotary evaporator
  7. customAfter purification by silica column chromatography, eluent

Sources & evidence

ORD record
ord-2783bba491654248a75744719c492a62
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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