Pyridine → HCID 12793262, compound

HRID 2082747Notes

Reaction equation

HRID 2082747 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[N:5][CH:4]=[C:3]1[C:19]([NH2:21])=O.N1C=CC=CC=1>P(Cl)(Cl)(Cl)=O>[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[N:5][CH:4]=[C:3]1[C:19]#[N:21]

Participants

4

Reactant 2

HCID 1049PyridineHCID 12793273HCID 12793273, compound

Product 1

HCID 12793262HCID 12793262, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1,6-Dihydro-6-oxo-2-(2-cyclopropylmethoxyphenyl)pyrimidine-5-carboxamide (13.6 g., 0.0476 mole) was added to a stirred, cold solution of pyridine (18.9 g., 0.24 mole) in phosphorus oxychloride (136 ml.), and the mixture heated under reflux for 15 minutes. The mixture was evaporated to dryness and the residue added to a mixture of ice and mthylene chloride. The mixture was neutralized with sodium bicarbonate. The methylene chloride layer was dried (sodium sulfate) and concentrated. To the residual oil was added 1N sodium hydroxide (15 ml.) and tetrahydrofuran (10 ml.). The mixture was allowed to stand at 25° for 18 hours. The mixture was washed with diethyl ether, filtered, and the filtrate acidified with acetic acid. The precipitate was recrystallized from toluene to give the title compound (7.6 g., 59.6%), m.p. 188°-190°. Two recrystallizations from ethyl acetate gave analytical material, m.p. 187°-189°.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 15 minutes
  3. customThe mixture was evaporated to dryness
  4. additionthe residue added to a mixture of ice and mthylene chloride
  5. dry with materialThe methylene chloride layer was dried (sodium sulfate)
  6. concentrationconcentrated
  7. additionTo the residual oil was added 1N sodium hydroxide (15 ml.) and tetrahydrofuran (10 ml.)
  8. washThe mixture was washed with diethyl ether
  9. filtrationfiltered
  10. customThe precipitate was recrystallized from toluene

Sources & evidence

ORD record
ord-58f9c258bff94e72a585f70818b8b4f4
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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