Acetonitrile → HCID 178499065, 화합물

HRID 1172053노트

반응식

HRID 1172053 반응식
[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9](N)[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([O:20][CH3:21])[C:14]=2[F:22])[N:6]=1)=[O:4].C(#N)C.N([O-])=[O:27].[Na+]>OS(O)(=O)=O>[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9]([OH:27])[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([O:20][CH3:21])[C:14]=2[F:22])[N:6]=1)=[O:4]

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 166568016-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-chloropyrimidine-4-carboxylic acid methyl esterHCID 23668193Sodium Nitrite

생성물 1

HCID 178499065HCID 178499065, 화합물수율 53%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-chloropyrimidine-4-carboxylic acid methyl ester (320 mg, 0.92 mmol, see U.S. Pat. No. 7,300,907 B2 for preparation) was dissolved in 10 mL 1M H2SO4 plus 4 mL acetonitrile, warmed to 75° C. and treated in portions with sodium nitrite (690 mg, 10 mmol) over 30 minutes. After stirring for 10 minutes more the mixture was cooled and the solid product was collected by filtration, washed well with water, and dried under vacuum at 80° C. to give 170 mg (53% yield) of 6-hydroxy-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-chloropyrimidine-4-carboxylic acid methyl ester MP 215-217° C.; MS m/z 346; 1H NMR (DMSO-d6): δ 7.47 (m, 2H), 3.94 (s, 3H), 3.91 (s, 3H), 3.34 (br s, 1H).

후처리

  1. temperaturewas cooled
  2. filtrationthe solid product was collected by filtration
  3. washwashed well with water
  4. customdried under vacuum at 80° C.

출처 및 근거

ORD 기록
ord-f2439570edf84fc7bd881d6b788bb82c
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07833940B2

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