4-Aminopyridine → 2-(pyridin-4-ylamino)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1062319Notes

Reaction equation

Cl.N=C1C=CN([C:9]2[N:10]=[CH:11][C:12]3[CH:18]=[C:17]([C:19]4[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[CH:20]=4)[C:16](=[O:29])[N:15]([CH2:30][CH3:31])[C:13]=3[N:14]=2)C=C1.C(=O)([O-])[O-].[K+].[K+].[NH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1>CS(C)=O>[N:42]1[CH:43]=[CH:44][C:39]([NH:38][C:9]2[N:10]=[CH:11][C:12]3[CH:18]=[C:17]([C:19]4[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[CH:20]=4)[C:16](=[O:29])[N:15]([CH2:30][CH3:31])[C:13]=3[N:14]=2)=[CH:40][CH:41]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 330 g (0.75 mol) of 2-(4-imino-4H-pyridin-1-yl)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride in 1.5 L of dimethylsulfoxide were added in one portion 114 g (0.825 mol) of powdered potassium carbonate, followed by the addition of a solution of 2.8 g (0.03 mol; 0.05 eq) 4-aminopyridine in 50 mL of dimethylsulfoxide. The reaction mixture was heated to 100° C., and aliquots were removed after 1 hour and analyzed by reverse phase high pressure liquid chromatography (RP-HPLC) (YMC-AQ column, 60:40 CH3CN/0.02 M SDS, pH 2.2, 1.0 mL/min, 254 nm). After 40 minutes, the reaction was shown to produce the title compound, plus a dimer-like compound of the formula

Workup

customaliquots were removed after 1 hour

Sources & evidence

ORD record: ord-bbbdce74eadf4d35a209ed81d1cc06ab
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960662B2

Reaction notes

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