Pyridine → HCID 178460290, compound

HRID 2286613Notes

Reaction equation

HRID 2286613 reaction equation
C([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:25]=[C:24]([OH:26])[C:23]([C:27]([OH:29])=[O:28])=[CH:22][N:21]=2)=[CH:16][CH:15]=1)=[O:12])[CH3:10])=O)(C)(C)C.N1C=CC=[CH:32][CH:31]=1.C(OC(=O)CC)(=O)CC>CO>[C:6]([NH:8][C@H:9]([C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:25]=[C:24]([OH:26])[C:23]([C:27]([OH:29])=[O:28])=[CH:22][N:21]=2)=[CH:18][CH:19]=1)=[O:12])[CH3:10])(=[O:5])[CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31263Propionic anhydrideHCID 178462203HCID 178462203, compound

Product 1

HCID 178460290HCID 178460290, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 1.90 g (6.3 mmol) of the above pyrimidine acid and 20 ml of pyridine is stirred at room temperature and 5 ml of propionic anhydride is added. After stirring 1 hr at room temperature, methanol (10 ml) is added and the mixture evaporated to a syrup in vacuo. Water is added to the residue, the pH is adjusted to 2.3 with dilute HCl, and the product filtered. After washing with water and drying gives 1.93 g of 2-[4-(N-propionyl-L-alanylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid; mp 247°-248° C. [α]D25 -81° (cl, pH 7).

Workup

  1. stirringAfter stirring 1 hr at room temperature
  2. customthe mixture evaporated to a syrup in vacuo
  3. additionWater is added to the residue
  4. filtrationthe product filtered
  5. washAfter washing with water
  6. customdrying

Sources & evidence

ORD record
ord-47feefb1e7fe4cc0aea0ca9852343d91
Source dataset
uspto-grants-1981_05
Patent number
US04267180

Reaction notes

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