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

HRID 1865913노트

반응식

HRID 1865913 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

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 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-21a91584572343e4b7ce219b4c388bba
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629350B2

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