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

HRID 2111824ノート

反応式

HRID 2111824 の反応式
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

参加物

7

反応物 5

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 201357721-(3-Bromopropyl)piperidine HydrobromideHCID 227367915-Amino-2-chloro-isonicotinic acidHCID 231511466-chloro-2-methyl-3-(4-hydroxyphenyl)pyrido[3,4-d]pyrimidin-4(3H)-one

生成物 1

HCID 117185676-chloro-2-methyl-3-{4-[3-(1-piperidinyl)propoxy]phenyl}pyrido[3,4-d]pyrimidin-4(3H)-one収率 60%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  1. customsynthesized
  2. distillationThe solvent was distilled off under reduced pressure
  3. distillationdistilled water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with distilled water
  7. dry with materialdried with anhydrous sodium sulfate

出典と根拠

ORDレコード
ord-40984d9c46d54c3cad60a5e5f67408f9
出典データセット
uspto-grants-2009_04
特許番号
US07521455B2

反応ノート

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