Phosphorus oxychloride → Ethyl 2-chloro-4-methylpyrimidine-5-carboxylate

HRID 1458630ノート

反応式

HRID 1458630 の反応式
O[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1.O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178469852Ethyl 2-hydroxy-4-methylpyrimidine-5-carboxylate

生成物 1

HCID 21220624Ethyl 2-chloro-4-methylpyrimidine-5-carboxylate収率 27%

実験手順

A solution of ethyl 2-hydroxy-4-methylpyrimidine-5-carboxylate (5 g, 27.5 mmol) and POCl3 (84 g, 550 mmol) was heated at reflux under N2 for 1 h. The reaction was cooled and concentrated. The residue was partitioned between CHCl3 and H2O and the organic layer was dried (Na2SO4), filtered, and concentrated to yield the title compound in a yield of 27% (1.5 g); 1HNMR (CDCl3) δ 9.04 (s, 1H), 4.42 (q, 2H), 2.85 (s, 3H), 1.43 (t, 3H).

後処理

  1. temperatureat reflux under N2 for 1 h
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. customThe residue was partitioned between CHCl3 and H2O
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-986248a5ba764f69baf697b3a073632e
出典データセット
uspto-grants-1998_12
特許番号
US05852028

反応ノート

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