Triethylamine → 4-Chloro-6-(2,4,6-trifluorophenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

HRID 1865915노트

반응식

HRID 1865915 반응식
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[F:13][C:14]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[C:15]=1[NH2:16].CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([NH:16][C:15]2[C:14]([F:13])=[CH:20][C:19]([F:21])=[CH:18][C:17]=2[F:22])[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 677652,4,6-TrifluoroanilineHCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

생성물 1

HCID 579781024-Chloro-6-(2,4,6-trifluorophenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde수율 87%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
50 °C

실험 절차

A solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde [Santilli, et al., J. Heterocycl. Chem. 1971, 8, 445-45] (1.0 g, 4.48 mmol) in CHCl3 (20 mL) was added 2,4,6-trifluoroaniline (0.735 mg, 5 mmol) followed by Et3N (0.94 mL, 6.72 mmol, 1.5 eq). The reaction mixture turned yellow and was heated to 50° C. for 8 h, 1 M aq Na2CO3 (50 mL) was added and the layers were separated. The organic layer was washed with 50 mL satd aq NaCl solution, dried through anhydrous MgSO4 and evaporated. The crude product was purified by flash chromatography to afford 1.3 g (87%) of pure 4-chloro-6-(2,4,6-trifluorophenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde. LC MS (m/e)=334.0 (MH+).

후처리

  1. customthe layers were separated
  2. washThe organic layer was washed with 50 mL
  3. dry with materialdried through anhydrous MgSO4
  4. customevaporated
  5. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-9cd7f6bb11c94e9681dcb34eef8d265d
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629350B2

반응 노트

불러오는 중…