Acetic Acid → HCID 178458305, compound

HRID 1978871Notes

Reaction equation

HRID 1978871 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])[N:5]=[C:4]([C:18]([NH2:20])=O)[CH:3]=1.C(O)(=O)C>P(Cl)(Cl)(Cl)=O>[C:18]([C:4]1[CH:3]=[C:2]([OH:1])[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])[N:5]=1)#[N:20]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 178458306HCID 178458306, compound2×

Product 1

HCID 178458305HCID 178458305, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent2×

Procedure

A stirred solution of 6-hydroxy-2-(2-propoxyphenyl)pyrimidine-4-carboxamide (0.50 g) in phosphoryl chloride (16 ml) was heated under reflux for 4 hours and then the reaction mixture was evaporated under reduced pressure to remove excess phosphoryl chloride. Water was added to the residue, which was extracted with chloroform (3×20 ml). The combined extracts were washed with water, dried (magnesium sulfate) and evaporated under reduced pressure to yield an oil which was heated on a steam bath with glacial acetic acid (15 ml) for 4 hours. The cooled reaction mixture was evaporated under reduced pressure to yield a crude product which was combined with further product similarly prepared from 6-hydroxy-2-(2-propoxyphenyl)-pyrimidine-4-carboxamide (0.82 g) and phosphoryl chloride (25 ml). The combined products were eluted from silica with ether:chloroform (9:1) and fractions containing product were combined and evaporated under reduced pressure to yield the title compound, 0.31 g, m.p. 135-6° C. (from isopropanol/ether).

Workup

  1. temperatureunder reflux for 4 hours
  2. customthe reaction mixture was evaporated under reduced pressure
  3. customto remove excess phosphoryl chloride
  4. additionWater was added to the residue, which
  5. extractionwas extracted with chloroform (3×20 ml)
  6. washThe combined extracts were washed with water
  7. dry with materialdried (magnesium sulfate)
  8. customevaporated under reduced pressure
  9. customto yield an oil which
  10. customThe cooled reaction mixture
  11. customwas evaporated under reduced pressure
  12. customto yield a crude product which
  13. washThe combined products were eluted from silica with ether:chloroform (9:1) and fractions
  14. additioncontaining product
  15. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ee7aee08941b4d8bbd398996597573e4
Source dataset
uspto-grants-2001_05
Patent number
US06239136B1

Reaction notes

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