Sodium hydride → 2-(2-Methoxy-pyrimidin-4-ylamino)-thiazole-5-carbonitrile

HRID 1241396ノート

反応式

HRID 1241396 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][N:6]=1.Cl[C:13]1[S:14][C:15]([C:18]#[N:19])=[CH:16][N:17]=1>C1COCC1>[CH3:3][O:4][C:5]1[N:10]=[C:9]([NH:11][C:13]2[S:14][C:15]([C:18]#[N:19])=[CH:16][N:17]=2)[CH:8]=[CH:7][N:6]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 1606792-O-MethylcytosineHCID 14852222-Chlorothiazole-5-carbonitrile

生成物 1

HCID 219346202-(2-Methoxy-pyrimidin-4-ylamino)-thiazole-5-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A flame dried flask under argon (g) was charged with sodium hydride (33 mg, 60% dispersion, 0.83 mmol) and 1.5 mL anhydrous THF. 2-Methoxy-pyrimidin-4-ylamine (26 mg, 0.21 mmol) was added slowly. After the resulting bubbling ceased, 2-chloro-thiazole-5-carbonitrile (30 mg, 0.21 mmol) was added and the reaction was heated to reflux. After 2 hours, the reaction was cooled to room temperature, the THF was removed in vacuo, and the mixture was diluted with water and adjusted to pH 7 with 1M HCl (aq). The resulting precipitate was filtered, washed with water and air dried. The resulting solid was purified by flash column chromatography (eluted with a gradient 85:15 hexane/EtOAc to EtOAc) to give a pure sample of the title compound. 1H-NMR (300 MHz, DMSO-d6) 12.61 (s, 1H), 8.36 (d, 1H, J=6.4 Hz), 6.73 (d, 1H, J=5.6 Hz), 4.02 (s, 3H). mp>250.

後処理

  1. customA flame dried flask under argon (g)
  2. customAfter the resulting bubbling
  3. temperaturethe reaction was heated to reflux
  4. customthe THF was removed in vacuo
  5. additionthe mixture was diluted with water
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with water and air
  8. customdried
  9. customThe resulting solid was purified by flash column chromatography (
  10. washeluted with a gradient 85:15 hexane/EtOAc to EtOAc)

出典と根拠

ORDレコード
ord-71c2775553174c24b528b7d4a05c9ef2
出典データセット
uspto-grants-2006_10
特許番号
US07115597B2

反応ノート

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