Acetic Anhydride → 6-chloro-2-methyl-3-{4-[3-(1-piperidinyl)propoxy]phenyl}pyrido[3,4-d]pyrimidin-4(3H)-one

HRID 2111824Notes

Reaction equation

NC1C(C(O)=O)=CC(Cl)=NC=1.C(OC(=O)C)(=O)C.[Cl:19][C:20]1[N:38]=[CH:37][C:23]2[N:24]=[C:25]([CH3:36])[N:26]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)[C:27](=[O:28])[C:22]=2[CH:21]=1.Br.Br[CH2:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:19][C:20]1[N:38]=[CH:37][C:23]2[N:24]=[C:25]([CH3:36])[N:26]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH2:41][CH2:42][CH2:43][N:44]4[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]4)=[CH:33][CH:34]=3)[C:27](=[O:28])[C:22]=2[CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Using 5-amino-4-carboxy-2-chloropyridine and acetic anhydride as starting materials, 6-chloro-2-methyl-3-(4-hydroxyphenyl)pyrido[3,4-d]pyrimidin-4(3H)-one synthesized according to Example 1-(1) and -(2) (52 mg, 0.18 mmol), 1-(3-bromopropyl)piperidine hydrobromide (78 mg, 0.27 mmol) and potassium carbonate (100 mg, 0.72 mmol) were mixed in dimethylformamide (1 mL) and stirred at 80° C. for 1 hour. The solvent was distilled off under reduced pressure, distilled water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with distilled water, and dried with anhydrous sodium sulfate. The title compound (45 mg, 60%) was obtained as colorless crystals by purifying with silica gel column chromatography (chloroform/methanol=30/1) and recrystallizing (ethanol).

Workup

customsynthesized
distillationThe solvent was distilled off under reduced pressure
distillationdistilled water
additionwas added
extractionthe mixture was extracted with ethyl acetate
washThe organic phase was washed with distilled water
dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record: ord-40984d9c46d54c3cad60a5e5f67408f9
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521455B2

Reaction notes

Loading…