Acetic Acid → HCID 19050657, compound

HRID 863758Notes

Reaction equation

HRID 863758 reaction equation
[Br:1][C:2]1[N:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[N:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[N:15]=2)[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(O)(=[O:26])C>>[Br:1][C:2]1[N:12]=[CH:11][CH:10]=[C:9]([C:13]([C:14]2[N:15]=[C:16]([O:22][CH3:23])[CH:17]=[C:18]([O:20][CH3:21])[N:19]=2)=[O:26])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 19050655HCID 19050655, compound

Product 1

HCID 19050657HCID 19050657, compound

Procedure

3.28 g of ethyl 2-bromo-4-[(4,6-dimethoxy-2-pyrimidinyl)methyl]nicotinate, 3.61 g of SeO2 and 100 ml of glacial acetic acid are combined under nitrogen, heated to 110° for 1.5 hrs and slowly cooled to RT still under nitrogen. The mixture is filtered, washed through with 10 ml of acetic acid and the filtrate evaporated to remove the acetic acid. 100 ml of methylene dichloride is added to the residue and the mixture washed twice with 100 ml of sat. aqueous NaHCO3. The CH2Cl2 phase is filtered and evaporated and the residue digested with 25 ml of 25% ethyl acetate/hexane at 50° for 15 mins. This solution is then poured onto a silica gel column and eluted with 3×125 ml of 25% ethyl acetate/hexane. Evaporation of combined fractions 1 and 2 yields the title product mp 98°-99°.

Workup

  1. temperatureheated to 110° for 1.5 hrs
  2. filtrationThe mixture is filtered
  3. washwashed through with 10 ml of acetic acid
  4. customthe filtrate evaporated
  5. customto remove the acetic acid
  6. addition100 ml of methylene dichloride is added to the residue
  7. washthe mixture washed twice with 100 ml of sat. aqueous NaHCO3
  8. filtrationThe CH2Cl2 phase is filtered
  9. customevaporated
  10. additionThis solution is then poured onto a silica gel column
  11. washeluted with 3×125 ml of 25% ethyl acetate/hexane
  12. customEvaporation of combined fractions 1 and 2

Sources & evidence

ORD record
ord-3cb9de192544489caa069dd6228b289f
Source dataset
uspto-grants-1996_10
Patent number
US05561101

Reaction notes

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