Diethyl Ether → 3-Bromo-5-(pyrimidin-4-yl)pyridin-2(1H)-one

HRID 1981505Notes

Reaction equation

HRID 1981505 reaction equation
[Br:1]Br.[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[N:5][CH:4]=1.CCOCC>C(O)(=O)C>[Br:1][C:11]1[C:12](=[O:15])[NH:13][CH:14]=[C:9]([C:6]2[CH:7]=[CH:8][N:3]=[CH:4][N:5]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 132766775-(Pyrimidin-4-yl)pyridin-2(1H)-one

Product 1

HCID 132766783-Bromo-5-(pyrimidin-4-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.7 g of bromine are added over a period of one minute to a solution of 4.5 g of 5-(4-pyrimidyl)-2(1H)-pyridone in 60 ml glacial acetic acid. The mixture is allowed to cool, stirred at RT for 1 hour and then poured into 100 ml of anhydrous ether and stirred for 30 minutes. The slurry is filtered and the filtered solid washed with ether and dried. The solid is suspended in 100 ml of H2O and the pH adjusted to about 6 with anhydrous K2CO3. The mixture is stirred for 15 minutes, filtered, the solid washed with H2O and briefly dried. The moist solid is added to 40 ml of 5% aqueous hydrochloric acid and the resultant mixture stirred for 30 minutes, diluted with an equal volume of isopropyl alcohol, stirred for an additional 10 minutes and filtered. The resulting solid is washed with isopropyl alcohol ether and dried, giving 3-bromo-5-(4-pyrimidyl)-2 (1H)-pyridone as a green powder, M.P>250° C.

Workup

  1. temperatureto cool
  2. stirringstirred for 30 minutes
  3. filtrationThe slurry is filtered
  4. washthe filtered solid washed with ether
  5. customdried
  6. stirringThe mixture is stirred for 15 minutes
  7. filtrationfiltered
  8. washthe solid washed with H2O
  9. custombriefly dried
  10. additionThe moist solid is added to 40 ml of 5% aqueous hydrochloric acid
  11. stirringthe resultant mixture stirred for 30 minutes
  12. additiondiluted with an equal volume of isopropyl alcohol
  13. stirringstirred for an additional 10 minutes
  14. filtrationfiltered
  15. washThe resulting solid is washed with isopropyl alcohol ether
  16. customdried

Sources & evidence

ORD record
ord-384d643e91144d388b0dacd182f4f61a
Source dataset
uspto-grants-1986_06
Patent number
US04593028

Reaction notes

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