Methyl chloroformate → 3-(1-methoxycarbonyl-1H-tetrazol-5-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidine

HRID 2259561Notes

Reaction equation

HRID 2259561 reaction equation
[NH:1]1[C:5]([C:6]2[C:11](=[O:12])[N:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]3=[N:8][CH:7]=2)=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:24]([O:26][CH3:27])=[O:25]>CN(C)C=O>[CH3:27][O:26][C:24]([N:1]1[C:5]([C:6]2[C:11](=[O:12])[N:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]3=[N:8][CH:7]=2)=[N:4][N:3]=[N:2]1)=[O:25]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 178515422HCID 178515422, compound

Product 1

HCID 190014463-(1-methoxycarbonyl-1H-tetrazol-5-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.07 g (0.005 moles) of 3-(1H-tetrazol-5-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidine; 45 ml of dimethylformamide, 0.75 g (0.0055 moles) of anhydrous potassium carbonate and 0.76 ml (0.01 moles) of methyl chloroformate was stirred at 80°-90° C. for 6 hours. The hot reaction mixture was filtered; the crystals precipitating from the filtrate were collected to obtain 0.32 g (23.5%) of the 1:1 ratio mixture of the title compounds, which on crystallization from ethanol gave the 3-(1-methoxycarbonyl-1H-tetrazol-5-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidine, m.p.: 182°-183° C.

Workup

  1. filtrationThe hot reaction mixture was filtered
  2. customthe crystals precipitating from the filtrate
  3. customwere collected
  4. customto obtain
  5. customon crystallization from ethanol

Sources & evidence

ORD record
ord-5a1f6d7eff0548b4845fa31b53a8f1a3
Source dataset
uspto-grants-1995_12
Patent number
US05475000

Reaction notes

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