2,4,6-Trimethylpyridine → HCID 135666683, compound

HRID 1388669Notes

Reaction equation

HRID 1388669 reaction equation
[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[N:11]=[CH:12][C:7]=2[C:6](=[O:21])[CH:5]=[CH:4]1)[CH3:2].[I-].[Li+].N1C(C)=CC(C)=CC=1C>CCCCCC>[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[N:11]=[CH:12][C:7]=2[C:6](=[O:21])[CH:5]=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 66321Lithium iodideHCID 13278599HCID 13278599, compound

Product 1

HCID 135666683HCID 135666683, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

C-4. 8-Ethyl-2-(4-hydroxyphenyl)pyrido[2,3-d]pyrimidin-5(8H)-one--A mixture containing 2.4 g of 8-ethyl-2-(4-methoxyphenyl)pyrido[2,3-d]pyrimidin-5(8H)-one, 8.1 g of anhydrous lithium iodide, 125 ml of collidine and one drop of dicyclohexyl-12-crown-4 was refluxed with stirring for 24 hours and then allowed to cool to room temperature. The reaction mixture was diluted with n-hexane (900 ml) to complete the precipitation of the product. The oily material that separated solidified on standing at room temperature. The solid was collected, washed with n-hexane and then dissolved in water. The water solution and washed with ether, acidified with hydrochloric acid and the resulting mixture was slurried, treated with an excess of sodium bicarbonate and again slurried. The solid was collected, washed with water and dried at 65° C. in vacuo to yield 1.85 g of 8-ethyl-2-(4-hydroxyphenyl)pyrido[2,3-d]pyrimidin-5(8H)-one, m.p. 320°-324° C. This product was combined with 12 g of product obtained in five other runs and the combined material was suspended in about 350 ml of boiling ethanol after which dimethylformamide was added portionwise until dissolution was complete. The hot solution was treated with decolorizing charcoal, filtered, and the filtrate cooled. The separated product was collected, washed with cold ethanol and dried in vacuo at 60° C. to produce 2.6 g of 8-ethyl-2-(4-hydroxyphenyl)pyrido[2,3-d]pyrimidin-5(8H)-one, m.p. 323°-325° C. The filtrate was stripped in vacuo, the solid residue was recrystallized from ethanoldimethylformamide to yield another 0.8 g of product, 8-ethyl-2-(4-hydroxyphenyl)pyrido[2,3-d]pyrimidin-5(8H)-one, m.p. 321°-322° C.

Workup

  1. temperaturewas refluxed
  2. customthe precipitation of the product
  3. customThe oily material that separated solidified
  4. customon standing at room temperature
  5. customThe solid was collected
  6. washwashed with n-hexane
  7. dissolutiondissolved in water
  8. washThe water solution and washed with ether
  9. additiontreated with an excess of sodium bicarbonate
  10. customThe solid was collected
  11. washwashed with water
  12. customdried at 65° C. in vacuo

Sources & evidence

ORD record
ord-cf55833873fe42abbc97da0b7b9384b0
Source dataset
uspto-grants-1984_02
Patent number
US04432981

Reaction notes

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