Formamide → 6-chloro-3H,4H-pyrido[3,4-d]pyrimidin-4-one

HRID 50826Notes

Reaction equation

HRID 50826 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.O.[CH:13]([NH2:15])=O>>[Cl:8][C:5]1[N:6]=[CH:7][C:2]2[N:1]=[CH:13][NH:15][C:9](=[O:11])[C:3]=2[CH:4]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 227367915-Amino-2-chloro-isonicotinic acid

Product 1

HCID 1354805256-chloro-3H,4H-pyrido[3,4-d]pyrimidin-4-oneYield 86%

Procedure

A solution of 5-amino-2-chloropyridine-4-carboxylic acid (8.1 g, 4.7 mmol) in formamide (100 mL) is stirred at 140° C. for 12 h. Dilution of the cooled mixture with water gives a precipitate of 6-chloro-3H-pyrido[3,4-d]pyrimidin-4-one (7.3 g, 86% yield). 1H NMR (DMSO) δ 12.73 (1H, m), 8.90 (1H, d, J=0.7 Hz), 8.23 (1H, s), 7.97 (1H, d, J=0.7 Hz).

Sources & evidence

ORD record
ord-a83c821d0d274b2b90e8ba6c05f3e65f
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

Loading…