Triphenyl phosphite → 4-[2-[4-(t-Butyl)phenyl]ethoxy]pteridine

HRID 1087002

반응식

HRID 1087002 반응식
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][N:3]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.ClCl.[C:36]([C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH2:47]O)=[CH:42][CH:41]=1)([CH3:39])([CH3:38])[CH3:37]>C(Cl)Cl.C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:36]([C:40]1[CH:41]=[CH:42][C:43]([CH2:46][CH2:47][O:1][C:2]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][N:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:44][CH:45]=1)([CH3:39])([CH3:38])[CH3:37]

참가 물질

8

반응물 4

HCID 7540Triphenyl phosphiteHCID 24526ChlorineHCID 79410p-tert-Butylphenethyl alcoholHCID 178518044HCID 178518044, 화합물

생성물 1

HCID 149961134-[2-[4-(t-Butyl)phenyl]ethoxy]pteridine

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 1140Toluene용매HCID 6344Dichloromethane용매3회

반응 조건

온도
-17.5 °C

실험 절차

To a suspension of 2 g of 4-hydroxypteridine in 20 mL of CH2Cl2 under nitrogen was added 1.2 g of 25 pyridine. The mixture was cooled to -30° C and over a 15 minute period a solution of 4.82 g of triphenyl phosphite in CH2Cl2 was added simultaneously with addition of chlorine gas. The mixture was stirred for one and one half hours while maintaining the temperature at -15 to -20° C. The mixture was then allowed to warm to 10° C., and a solution of 2.67 g of 2-[4-(t-butyl)phenyl]ethanol in CH2Cl2 was added. The resulting mixture was refluxed for 45 minutes, then cooled and diluted into toluene. The toluene solution was washed with dilute base, then filtered through phase separating paper and concentrated in vacuo. The resulting bluish oil was adsorbed onto silica gel and chromatographed (silica gel, CH2Cl2 →80% CH2Cl2, 20% EtOAc). Fractions containing the major product were combined. The product was then recrystallized from petroleum ether/CH2Cl2. Yield 60 mg. M.P. 149° C.

후처리

  1. temperatureto warm to 10° C.
  2. temperatureThe resulting mixture was refluxed for 45 minutes
  3. temperaturecooled
  4. washThe toluene solution was washed
  5. additionwith dilute base
  6. filtrationfiltered through phase
  7. customseparating paper
  8. concentrationconcentrated in vacuo
  9. customchromatographed (silica gel, CH2Cl2 →80% CH2Cl2, 20% EtOAc)
  10. additionFractions containing the major product
  11. customThe product was then recrystallized from petroleum ether/CH2Cl2

출처 및 근거

ORD 기록
ord-c7b84f61f4e3445b8876ade0e5030088
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05034393

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