Phosphorus oxychloride → 4-Chloro-6-(2-furanyl)-2-pyrimidinamine

HRID 583813ノート

反応式

HRID 583813 の反応式
[NH2:1][C:2]1[N:7]=[C:6](O)[CH:5]=[C:4]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:16]>>[NH2:1][C:2]1[N:7]=[C:6]([Cl:16])[CH:5]=[C:4]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178508968HCID 178508968、化合物

生成物 1

HCID 223243064-Chloro-6-(2-furanyl)-2-pyrimidinamine

実験手順

A solution of 2-amino-4-hydroxy-6-(2-furyl)pyrimidine (1.40 g, 7.9 mmol) in POCl3 (4 mL) was refluxed under argon for 2 h. The POCl3 was distilled; the residue was diluted with EtOAc and poured over iced saturated NaHCO3. The layers were separated and the aqueous was extracted with EtOAc (100 mL). The combined extracts was washed with saturated NaCl, dried (MgSO4), and the solvent removed at reduced pressure to afford 0.5 g of crude product, which was used without further purification. TLC (20% EtOAc/80% hexane) Rf 0.26; 1H-NMR (DMSO-d6) δ 6.68 (dd, J=1.7, 3.4 Hz, 1H), 6.94 (s, 1H), 7.25 (dd, J=1, 3.7 Hz, 1H), 7.91 (dd, J=0.8, 1.9 Hz, 1H).

後処理

  1. distillationThe POCl3 was distilled
  2. additionthe residue was diluted with EtOAc
  3. additionpoured over iced saturated NaHCO3
  4. customThe layers were separated
  5. extractionthe aqueous was extracted with EtOAc (100 mL)
  6. washThe combined extracts was washed with saturated NaCl
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed at reduced pressure

出典と根拠

ORDレコード
ord-cf611ab3098548c68a4b63b88e9c7030
出典データセット
uspto-grants-2005_08
特許番号
US06924290B2

反応ノート

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