Dimethyl Sulfoxide → HCID 13131705, compound

HRID 1262627Notes

Reaction equation

HRID 1262627 reaction equation
Br[C:2]1(Br)[C:7]2=[N:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[C:11](=[O:12])[N:6]2[CH:5]([CH3:16])[CH2:4][CH2:3]1.CS(C)=O.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CN(C)C1C=CC=CC=1>O>[NH:22]([C:2]1[C:7]2=[N:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[C:11](=[O:12])[N:6]2[CH:5]([CH3:16])[CH2:4][CH:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 949N,N-DimethylanilineHCID 6115AnilineHCID 13312949HCID 13312949, compound

Product 1

HCID 13131705HCID 13131705, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.83 g. (0.005 moles) of 9,9-dibromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid are dissolved in 5 ml. of dimethyl sulfoxide. To the solution 0.5 ml. (0.0055 moles) of aniline and 1.3 ml. (0.01 moles) of N,N-dimethylaniline are added. The reaction mixture is allowed to stand for three days, whereupon it is poured onto 20 ml. of water. The crystals are filtered off, washed with a small amount of water, dried and recrystallized from acetonitrile. 0.83 g. (55.8%) of 9-anilino-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid are obtained, melting at 169° to 170° C.

Workup

  1. additionis poured onto 20 ml
  2. filtrationThe crystals are filtered off
  3. washwashed with a small amount of water
  4. customdried
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-94f1401314c341e288482838235103f0
Source dataset
uspto-grants-1984_06
Patent number
US04452982

Reaction notes

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