2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → 2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methoxy-4-pyrimidone

HRID 358467ノート

反応式

HRID 358467 の反応式
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[CH3:3].CS[C:17]1[NH:22][C:21](=[O:23])[C:20]([O:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:19][N:18]=1>N1C=CC=CC=1>[CH3:3][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:17]2[NH:22][C:21](=[O:23])[C:20]([O:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:19][N:18]=2)[N:9]=1)[CH3:1]

参加物

4

反応物 2

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 133735192-Methylthio-5-(3-pyridyl)methoxy-4-pyrimidone

生成物 1

HCID 133735062-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methoxy-4-pyrimidone

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A reaction mixture was prepared from 1.26 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine and 1.36 g. of 2-methylthio-5-(3-pyridyl)methoxy-4-pyrimidone in 20 ml. of pyridine. The reaction mixture was heated to reflux temperature for about 2 days. The pyridine was then removed by evaporation in vacuo and the resulting residue subjected to high pressure liquid chromatography over silica. Fractions shown by tlc to contain the desired compound were combined and the combined fractions rechromatographed on a silica preparative plate using 3% ammoniated ethanol as the solvent. 2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methoxy-4-pyrimidone free base thus obtained was converted to the trihydrochloride salt by standard procedures. Recrystallization of the crude trihydrochloride salt from ethanol yielded 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methoxy-4-pyrimidone trihydrochloride melting at 183°-185° C.

後処理

  1. customA reaction mixture was prepared from 1.26 g
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux temperature for about 2 days
  4. customThe pyridine was then removed by evaporation in vacuo
  5. customthe combined fractions rechromatographed on a silica preparative plate

出典と根拠

ORDレコード
ord-dea562174826482aabf35801f85916cc
出典データセット
uspto-grants-1984_08
特許番号
US04468399

反応ノート

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