2,6-Diaminopyridine → N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

HRID 404776

반응식

HRID 404776 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[Cl:9][C:10]1[CH:15]=[C:14](Cl)[N:13]=[CH:12][N:11]=1>C(O)CCC>[Cl:9][C:10]1[N:11]=[CH:12][N:13]=[C:14]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=2)[CH:15]=1

참가 물질

4

반응물 2

HCID 88612,6-DiaminopyridineHCID 709434,6-Dichloropyrimidine

생성물 1

HCID 57708264N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine수율 32.7%

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2,6-diaminopyridine (1.530 g, 14.020 mmol) and 4,6-dichloropyrimidine (2.610 g, 17.519 mmol) in 15 mL of n-butanol in a sealed vial was heated at 100° C. for 72 h. The dark brown sample was cooled, was concentrated to remove most of the n-butanol, and was then partitioned between EtOAc and sat. NaHCO3 solution. An emulsion formed, the sample was filtered through a pad of Celite and the layers were separated. The organic extract was washed with sat. KH2PO4 and brine solutions, was dried (MgSO4), was filtered and was concentrated to brown oily-solid. The sample was suspended into 50 mL of CH2Cl2, was cooled and was filtered to give 1.017 g of N-(6-chloro-pyrimidin-4-yl)-pyridine-2,6-diamine as yellow-orange solid. MS (ES) (m/z) 222/224 (M+1, 100/63%). TLC (SiO2, 50% EtOAc in hexanes): Rf 0.33.

후처리

  1. temperatureThe dark brown sample was cooled
  2. concentrationwas concentrated
  3. customto remove most of the n-butanol
  4. customwas then partitioned between EtOAc and sat. NaHCO3 solution
  5. customAn emulsion formed
  6. filtrationthe sample was filtered through a pad of Celite
  7. customthe layers were separated
  8. extractionThe organic extract
  9. washwas washed with sat. KH2PO4 and brine solutions
  10. dry with materialwas dried (MgSO4)
  11. filtrationwas filtered
  12. concentrationwas concentrated to brown oily-solid
  13. temperaturewas cooled
  14. filtrationwas filtered

출처 및 근거

ORD 기록
ord-d7e4a78f983d4bbd92b5facf535089b1
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748606B2

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