Ethyl hexanoate → 7-Butyl-8-hydroxy-5-phenylpyrido[2,3-b]pyrazin-6(5H)-one

HRID 1583313Notes

Reaction equation

HRID 1583313 reaction equation
[C:1]1([NH:7][C:8]2[C:13]([C:14]([O:16]C)=O)=[N:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](OCC)(=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].CC(C)([O-])C.[K+]>>[CH2:20]([C:19]1[C:18](=[O:24])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2=[N:9][CH:10]=[CH:11][N:12]=[C:13]2[C:14]=1[OH:16])[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 31265Ethyl hexanoateHCID 13370930Methyl 3-anilinopyrazine-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 546800437-Butyl-8-hydroxy-5-phenylpyrido[2,3-b]pyrazin-6(5H)-one

Procedure

A mixture of 3.5 g. of methyl 2-phenylamino-3-pyrazine carboxylate, 30 ml. of ethyl caproate and 4 g. of potassium tertiary butoxide is stirred and heated under nitrogen at 150°-160° for one and a half hours. The reaction mixture is poured on ice, extracted with ethyl acetate and the ethyl acetate extracts washed with water. The combined aqueous layers are acidified to pH 5.5 with dilute hydrochloric acid and the solid filtered. Recrystallization from ethyl acetate-hexane yields the product of this example as a colorless solid; m.p. 183°-185° C.

Workup

  1. additionA mixture of 3.5 g
  2. temperatureheated under nitrogen at 150°-160° for one and a half hours
  3. additionThe reaction mixture is poured on ice
  4. extractionextracted with ethyl acetate
  5. washthe ethyl acetate extracts washed with water
  6. filtrationthe solid filtered
  7. customRecrystallization from ethyl acetate-hexane
  8. customyields the product of this example as a colorless solid

Sources & evidence

ORD record
ord-343a1db5ed8846fd84b3579c44099945
Source dataset
uspto-grants-1985_11
Patent number
US04551463

Reaction notes

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