Hydrochloric Acid → HCID 13369416, compound

HRID 443399Notes

Reaction equation

HRID 443399 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].C(O)C.[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>ClCCl>[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]([N:23]([CH3:22])[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 313Hydrochloric AcidHCID 702EthanolHCID 7515N-MethylanilineHCID 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 13369416HCID 13369416, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g. (0.016 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 50 ml. of ethanol. To the solution 3.5 ml. (0.032 mole) of N-methyl-aniline are added and the reaction mixture is boiled for 8-9 hours in a nitrogen gas atmosphere. 50 ml. or 5% by weight hydrochloric acid solution is then added to the solution and shaken out three times with 25 ml. of dichloromethane. The combined organic layers are dried above calcinated sodium sulfate and evaporated at reduced pressure. The residue is dark oil which crystallizes upon the addition of some methanol. 3.0 g. (55.2%) of 6-methyl-9-(N-methyl-anilino)-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester are obtained. Melting point: 175°-178° C.

Workup

  1. customThe combined organic layers are dried
  2. customevaporated at reduced pressure
  3. customcrystallizes upon the addition of some methanol

Sources & evidence

ORD record
ord-6aa4a27112bc4a27b68418fad7bab5cd
Source dataset
uspto-grants-1981_04
Patent number
US04260612

Reaction notes

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