Phosphorus oxychloride → 2,5-Diamino-4,6-dichloropyrimidine

HRID 1396749ノート

反応式

HRID 1396749 の反応式
[ClH:1].[NH2:2][C:3]1[N:8]=[C:7](O)[C:6]([NH2:10])=[C:5](O)[N:4]=1.P(Cl)(Cl)([Cl:14])=O>[Cl-].C([N+](CC)(CC)CC)C>[Cl:1][C:5]1[C:6]([NH2:10])=[C:7]([Cl:14])[N:8]=[C:3]([NH2:2])[N:4]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178479162HCID 178479162、化合物

生成物 1

HCID 3010392,5-Diamino-4,6-dichloropyrimidine収率 64%

試薬・触媒・溶媒 1

HCID 5946Tetraethylammonium Chloride触媒

反応条件

温度
105 °C

実験手順

A suspension of 2,5-diamino-4,6-dihydroxypyrimidine hydrochloride (5.0 g, 28 mmol) and tetraethylammonium chloride (27.8 g, 0.167 mmol) in phosphorus oxychloride (80 ml) was heated at 105° C. for 20 hours. After cooling down to room temperature, the excess phosphorus oxychloride was distilled off under vacuum. The reaction mixture was poured into ice water and the pH was adjusted to 4, and the mixture was stirred for 1 hour at 50° C. The pH was adjusted to 7 and the product was extracted with ethyl acetate, washed with a saturated NaHCO3 solution, brine and dried over Na2SO4. After removing the solvents under reduced pressure, the residue was purified by flash chromatography on silica (CH2Cl2/MeOH 50:1), affording the title compound (3.21 g, 64%).

後処理

  1. temperatureAfter cooling down to room temperature
  2. distillationthe excess phosphorus oxychloride was distilled off under vacuum
  3. additionThe reaction mixture was poured into ice water
  4. extractionthe product was extracted with ethyl acetate
  5. washwashed with a saturated NaHCO3 solution, brine
  6. dry with materialdried over Na2SO4
  7. customAfter removing the solvents under reduced pressure
  8. customthe residue was purified by flash chromatography on silica (CH2Cl2/MeOH 50:1)

出典と根拠

ORDレコード
ord-6f30d1aa0a9745bf8af50932bd1738a1
出典データセット
uspto-grants-2014_12
特許番号
US08901132B2

反応ノート

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