p-Toluenesulfonic acid → 9-Hydroxy-3-(2-hydroxyethyl)-2-methylpyrido[1,2-a]pyrimidin-4-one

HRID 2241081Notes

Reaction equation

HRID 2241081 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]([CH:12]1[CH2:17][CH2:16][O:15][C:13]1=[O:14])(=O)[CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[OH:8][C:7]1[C:2]2=[N:1][C:9]([CH3:10])=[C:12]([CH2:17][CH2:16][OH:15])[C:13](=[O:14])[N:3]2[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 106012-AcetylbutyrolactoneHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 166560309-Hydroxy-3-(2-hydroxyethyl)-2-methylpyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

During chemical development this process was altered. 2-Amino-3-hydroxypyridine was reacted with 2-acetyl-butyrolactone in the presence of p-toluenesulfonic acid in xylene to yield 9-hydroxy-3-(2-hydroxyethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; this product proved to be poorly soluble in xylene resulting in deposit formation on the wall of the reaction vessel and discoloration of the reaction mixture to black.

Sources & evidence

ORD record
ord-ca54f693271e48ac9014840f257d2981
Source dataset
uspto-grants-2010_05
Patent number
US07723518B2

Reaction notes

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