Dimethyl Sulfoxide → HCID 23467117, compound

HRID 443398Notes

Reaction equation

HRID 443398 reaction equation
Br[CH: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][CH2:3]1.CS(C)=O.[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>CO>[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][CH:2]2[C:7]3=[N:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[C:11](=[O:12])[N:6]3[CH:5]([CH3:16])[CH2:4][CH2:3]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 78074-BromoanilineHCID 15584879HCID 15584879, compound

Product 1

HCID 23467117HCID 23467117, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.9 g. (0.01 mole) of (-)-9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ([α]D20 =-105°, c=2, methanol) are dissolved in 5 ml. of dimethyl-sulfoxide and 3.8 g. (0.022 mole) of p-bromo-aniline are added. The solution is allowed to stand for 3 days at room temperature in an open vessel. 20 ml. of methanol are then added to the reaction mixture. The precipitated crystals are then filtered and washed with methanol. 1.7 g. (45.2%) of (-)-9-(4-bromo-anilino)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid is obtained. Melting point: 210°-211° C.

Workup

  1. filtrationThe precipitated crystals are then filtered
  2. washwashed with methanol

Sources & evidence

ORD record
ord-07da5f4a97834ea8a5a1a8e735799498
Source dataset
uspto-grants-1981_04
Patent number
US04260612

Reaction notes

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