Pyridine → HCID 178498585, compound

HRID 1755911Notes

Reaction equation

HRID 1755911 reaction equation
[OH:1][CH2:2][C:3]1[N:16]=[C:6]2[NH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:10](=[O:11])[N:5]2[N:4]=1.N1C=CC=CC=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>ClCCl>[C:23]([O:1][CH2:2][C:3]1[N:16]=[C:6]2[NH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:10](=[O:11])[N:5]2[N:4]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178498587HCID 178498587, compound

Product 1

HCID 178498585HCID 178498585, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

Methyl 4,7-dihydro-2-(hydroxymethyl)-7-oxo-s-triazolo[1,5-a]pyrimidine-5-carboxylate (2.5 g) (11.1 mmol) are suspended in 20 ml of dichloromethane. After the addition of 1.76 g (22.3 mmol) of pyridine and 2.27 g (22.2 mmol) of acetic anhydride the mixture is stirred at 55° C. for 8 hours. The mixture is concentrated in a vacuum and the product is precipitated with diethyl ether. After recrystallization from methanol there are obtained 1.2 g of methyl 2-(acetoxymethyl)-4,7-dihydro-7-oxo-s-triazolo[1,5-a]pyrimidine-5-carboxylate as white crystals of melting point 260° C.

Workup

  1. concentrationThe mixture is concentrated in a vacuum
  2. customthe product is precipitated with diethyl ether
  3. customAfter recrystallization from methanol

Sources & evidence

ORD record
ord-806e1a45304f4eba80f593513216625c
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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