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

HRID 1865913ノート

反応式

HRID 1865913 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

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 gram (hereinafter “g”), 4.48 millimoles (hereinafter “mmol”)) in CHCl3 (20 milliliters (hereinafter “mL”)) was added 2,4,6-tri-fluoroaniline (0.735 g, 5 mmol) followed by Et3N (0.94 mL, 6.72 mmol, 1.5 equivalents (hereinafter “eq”)). The reaction mixture turned yellow and was heated at 50° C. for 8 hours (hereinafter “h”), 1 M aq Na2CO3 solution (50 mL) was added and the layers were separated. The organic layer was washed with 50 ml sat'd. aqueous (hereinafter “satd aq”) NaCl solution, dried through anhydrous MgSO4 and evaporated. The crude product was purified by flash chromatography (Hex/AcOEt=95/5) to afford 1.3 g (87%) of pure 4-chloro-6-(2,4,6-trifluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde.

後処理

  1. additionwas added
  2. customthe layers were separated
  3. washThe organic layer was washed with 50 ml
  4. dry with materialdried through anhydrous MgSO4
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (Hex/AcOEt=95/5)

出典と根拠

ORDレコード
ord-21a91584572343e4b7ce219b4c388bba
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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