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

HRID 2403102

반응식

HRID 2403102 반응식
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

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 1358788822-(4-Chlorophenyl)-6-hydroxypyrimidine-4-carboxylic acid2회

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-75cf40bba2014aaba2a68a4a7b7ecb16
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802597B2

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