Acetonitrile → 6-Amino-2-(4-chlorophenyl)pyrimidine-4-carboxylic acid

HRID 249662

反応式

HRID 249662 の反応式
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=O)[CH:16]=[C:17]([C:19]([OH:21])=[O:20])[N:18]=2)=[CH:9][CH:8]=1.C(#[N:25])C>O>[NH2:25][C:15]1[N:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=2)[N:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=1

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 1358788822-(4-Chlorophenyl)-6-hydroxypyrimidine-4-carboxylic acid2 回

生成物 1

HCID 468639856-Amino-2-(4-chlorophenyl)pyrimidine-4-carboxylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

To phosphorus oxychloride (180 mL) was added 2-(4-chlorophenyl)-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (i.e. the product of Step A) (81.81 g, 326 mmol). The mixture was heated to 90° C. for 2.5 h. After cooling to room temperature the reaction mixture was slowly added to 1:2 acetonitrile:water (1.5 L) while keeping the temperature between 35 and 45° C. After the reaction mixture was stirred at room temperature for 30 minutes the resulting solid was isolated by filtration and washed with water. The solid was then combined with aqueous ammonia (5%, 2.1 L) and heated to 80° C. for 18 h. After 2 days at room temperature the solid was isolated by filtration and washed with water. A second crop was obtained by cooling the filtrate and refiltering. The combined solids were dried to afford the title compound (58.8 g).

後処理

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customthe temperature between 35 and 45° C
  3. customwas isolated by filtration
  4. washwashed with water
  5. temperatureheated to 80° C. for 18 h
  6. customAfter 2 days at room temperature the solid was isolated by filtration
  7. washwashed with water
  8. customA second crop was obtained
  9. temperatureby cooling the filtrate and refiltering
  10. customThe combined solids were dried

出典と根拠

ORDレコード
ord-1098f0148d4746dd829304c89117beb2
出典データセット
uspto-grants-2011_01
特許番号
US07863220B2

関連ノート

読み込み中…