Dimethyl Sulfoxide → 9-(phenyl-amino)-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester

HRID 443391Notes

Reaction equation

HRID 443391 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]([CH3:18])[CH2:14][CH2:15][CH:16](Br)[C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2].CS(C)=O.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]([CH3:18])[CH2:14][CH:15]=[C:16]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 6115AnilineHCID 134472569-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester

Product 1

HCID 133694119-(phenyl-amino)-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl esterYield 59.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

40.0 g. (0.127 mole) of 9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester are dissolved in 80 ml. of dimethylsulfoxide and 26 ml. (0.285 mole) of aniline are added. The solution is allowed to stand at room temperature for 3-4 days. The mixture is then diluted with 100 ml. of water, shaken out with 3×50 ml. of benzene. The combined organic layers are dried with calcinated sodium sulfate and evaporated in vacuo. The residue is recrystallized from ethanol and thus 24.5 g. (59.3%) of 9-(phenyl-amino)-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic ethyl ester is obtained, melting point: 119°-120° C.

Workup

  1. additionThe mixture is then diluted with 100 ml
  2. dry with materialThe combined organic layers are dried with calcinated sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue is recrystallized from ethanol and thus 24.5 g

Sources & evidence

ORD record
ord-306929a9f1824e4e8d397cbbfe6663e5
Source dataset
uspto-grants-1981_04
Patent number
US04260612

Reaction notes

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