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Potassium Carbonate → 3-Ethyl-5-[2-(6-methoxy-pyridin-3-ylamino)-pyrimidin-4-yl]-4-methyl-3H-thiazol-2-one

HRID 601445
ノート
印刷プレビュー

反応式

HRID 601445 の反応式
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[S:11][C:10](=[O:12])[N:9]([CH2:13][CH3:14])[C:8]=1[CH3:15])=O.[N+]([O-])(O)=O.[CH3:21][O:22][C:23]1[N:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[NH:31])=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>COCCO>[CH2:13]([N:9]1[C:8]([CH3:15])=[C:7]([C:5]2[CH:4]=[CH:3][N:32]=[C:30]([NH:29][C:26]3[CH:27]=[N:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)[N:31]=2)[S:11][C:10]1=[O:12])[CH3:14]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 672738395-(3-Dimethylamino-acryloyl)-3-ethyl-4-methyl-3H-thiazol-2-oneHCID 1784923121-(6-Methoxypyridin-3-yl)guanidine nitrate

生成物 1

HCID 114051633-Ethyl-5-[2-(6-methoxy-pyridin-3-ylamino)-pyrimidin-4-yl]-4-methyl-3H-thiazol-2-one収率 39.4%

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol
溶媒

反応条件

温度
120 °C

実験手順

5-(3-Dimethylamino-acryloyl)-3-ethyl-4-methyl-3H-thiazol-2-one (80 mg, 0.333 mmol), N-(6-methoxy-pyridin-3-yl)-guanidine nitrate (76 mg, 0.333 mmol) and K2CO3 (185 mg, 1.332 mmol) were combined in of 2-methoxyethanol (4 mL) and the mixture was heated at 120° C. for 22 h. After cooling, the inorganics were filtered off and the filtrate was concentrated to dryness. The crude product was purified by SiO2 gel chromatography. Pooling of the desired fractions afforded the title compound (45 mg, 39%). 13C-NMR (d6-DMSO) δ: 14.5, 14.7, 37.3, 53.7, 109.0, 110.3, 128.4, 131.82, 132.4, 137.8, 138.4, 152.7, 159.5, 160.3, 164.7, 170.1. Remaining analytical data in Table 2.

後処理

  1. temperatureAfter cooling
  2. filtrationthe inorganics were filtered off
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe crude product was purified by SiO2 gel chromatography

出典と根拠

ORDレコード
ord-9f436ab52e6a4ffbad7dcc65bfad9eb2
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902361B2

反応ノート

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