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

HRID 1865915ノート

反応式

HRID 1865915 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
50 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-9cd7f6bb11c94e9681dcb34eef8d265d
出典データセット
uspto-grants-2009_12
特許番号
US07629350B2

反応ノート

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