Ammonia → HCID 22484549, 화합물

HRID 398231

반응식

HRID 398231 반응식
N.[Na].C([N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([O:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:13]=2[CH:12]=[CH:11]1)C1C=CC=CC=1>CCOCC>[CH:20]1([O:19][C:18]2[C:13]3[CH:12]=[CH:11][NH:10][C:14]=3[N:15]=[CH:16][N:17]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 5360545SodiumHCID 224845557-Benzyl-4-cyclohexyloxy-7H-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 22484549HCID 22484549, 화합물수율 9.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-78 °C

실험 절차

To liquid ammonia (6.0 mL) at −78° C. was added 33 mg (1.43 mmol) sodium metal and the resulting dark blue solution stirred at −78° C. 10 min. A solution of 75 mg (0.244 mmol) of the product from Method M in 3.0 mL of ether was added dropwise over a 5 min period. The resulting solution stirred at −78° C. for 1 h followed by quenching upon addition of 500 mg of solid ammonium chloride. After evaporation at room temperature, the residual solid was triturated with 25 mL of ethylacetate containing 1 mL of acetic acid for 1 h. Filtration and concentration in vacuo afforded crude material which was purified by preparative thin layer chromatography (silica-gel; 2:1 ethyl acetate/hexanes) to produce 5 mg of the title compound. 1H NMR (400 MHz) (CDCl3) δ: 1.27-1.35 (m, 6H), 1.62-1.67 (m, 4H), 5.30-5.36 (m, 1H), 6.55 (d, 1H, J=3.2 Hz), 7.11 (d, 1H, J=3.2 Hz), 8.37 (br s 1H). LRMS: 218.2 (M+1).

후처리

  1. custom10 min
  2. stirringThe resulting solution stirred at −78° C. for 1 h
  3. customby quenching upon addition of 500 mg of solid ammonium chloride
  4. customAfter evaporation at room temperature
  5. customthe residual solid was triturated with 25 mL of ethylacetate containing 1 mL of acetic acid for 1 h
  6. filtrationFiltration and concentration in vacuo
  7. customafforded crude material which
  8. customwas purified by preparative thin layer chromatography (silica-gel; 2:1 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-a9b0e42275f2498881833c2d443e9a6a
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610847B2

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