Triethylamine → HCID 9860535, 화합물

HRID 1655935노트

반응식

HRID 1655935 반응식
Cl[C:2]1[N:10]=[C:9]([NH:11]C=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][O:20][CH:21]([CH3:23])[CH3:22].C(N(CC)CC)C>[Pd].CO>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[O:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][O:20][CH:21]([CH3:23])[CH3:22])=[CH:2][N:10]=1

참가 물질

5

반응물 2

HCID 8471TriethylamineHCID 19789735HCID 19789735, 화합물

생성물 1

HCID 9860535HCID 9860535, 화합물수율 41.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

반응 조건

온도
20 °C

실험 절차

A mixture of 6-chloro-2-formamido-9-[3-(isopropoxymethoxy)propoxy]purine (1.86 g, 5.40 mmol), 10% palladium on charcoal (190 mg), triethylamine (3.8 ml, 27 mmol) and methanol (30 ml) was stirred under an atmosphere of hydrogen at 20° C. for 4 hr. The suspension was filtered, the catalyst washed with chloroform and the combined filtrates evaporated under reduced pressure. The residue was dissolved in dichloromethane (50 ml), washed with saturated brine-water (2:1), dried (magnesium sulphate) and evaporated. The residue was dissolved in 0.5M sodium methoxide in methanol (21.6 ml) and heated at reflux for 1 hr. The solution was taken to neutrality using AMBERLITE IR 120(H) and evaporated. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (20:1) affording the title compound (630 mg, 41%) after recrystallisation from acetone-hexane; νmax (KBr) 3333, 3192, 1661, 1623, 1577, 1516, 1433 cm-1 ; δH [(CD3 )2SO] 1.09 (6H, d, J 6.05 Hz, 2×CH3), 1.95 (2H, quintet, J 6.6 and 6.3 Hz, CH2CH2CH2), 3.63 (2H, t, J=6.3 Hz, CH2OC), 3.77 (1H, septet, J=6.0 Hz, CH), 4.39 (2H, J=6.6 Hz, CH2ON), 4.64 (2H, s, OCH2O), 6.69 (2H, br.s, D2O exchangeable, NH2), 8.31 (1H, s, H-8), 8.59 (1H, s, H-6). Found: C, 51.21; H, 6.84; N, 24.82%; C12H19N5O3 requires: C, 51.22; H, 6.82; N, 24.89%.

후처리

  1. filtrationThe suspension was filtered
  2. washthe catalyst washed with chloroform
  3. customthe combined filtrates evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (50 ml)
  5. washwashed with saturated brine-water (2:1)
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated
  8. dissolutionThe residue was dissolved in 0.5M sodium methoxide in methanol (21.6 ml)
  9. temperatureheated
  10. temperatureat reflux for 1 hr
  11. customevaporated
  12. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol (20:1)

출처 및 근거

ORD 기록
ord-c28184a4e43b4a118e2e87d671ffa45d
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05252575

반응 노트

불러오는 중…