Adenine → 2-(6-Aminopurin-9-yl)ethanol

HRID 336057

반응식

HRID 336057 반응식
[H-].[Na+].[N:3]1[C:11]([NH2:12])=[C:10]2[C:6]([N:7]=[CH:8][NH:9]2)=[N:5][CH:4]=1.Br[CH2:14][CH2:15][O:16]C(=O)C1C=CC=CC=1.N>CN(C=O)C.CO>[OH:16][CH2:15][CH2:14][N:7]1[CH:8]=[N:9][C:10]2[C:6]1=[N:5][CH:4]=[N:3][C:11]=2[NH2:12]

참가 물질

7

반응물 4

HCID 190AdenineHCID 222AmmoniaHCID 24758Sodium hydrideHCID 5230902-Bromoethyl Benzoate

생성물 1

HCID 2426522-(6-Aminopurin-9-yl)ethanol

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a suspension of 60% NaH in mineral oil (1.70 g, 42.57 mmol) in anhydrous DMF (120 mL) was added adenine (5.23 g, 38.70 mmol) under argon, and the mixture was heated at 60° C. for 1 h. 2-Bromoethylbenzoate (9.2 mL, 58.06 mmol) was added dropwise at 60° C., and the reaction was stirred at this temperature for 16 h. The mixture was then filtered to remove insoluble materiel, the filtrate was evaporated under reduced pressure and co-evaporated three times with toluene. The residue was triturated with EtOAc then filtered to give a white solid, which was immediately resuspended in a saturated ammonia solution in MeOH (400 mL). The reaction mixture was stirred for 14 h at room temperature, and then methanol was removed under reduced pressure. Recrystallization from EtOH afforded compound 2 (5.87 g, 85%): mp 236° C. (Lit. 238-239° C.); 1H NMR (DMSO-d6): 8.13 (s, 1H, H-2), 8.10 (s, 1H, H-8), 7.23 (bs, 2H, NH2), 5.05 (bs, 1H, OH), 4.19 (t, J=5.2 Hz, 2H, CH2O), 3.71 (t, J=5.2 Hz, 2H, CH2N). 13C NMR (DMSO-d6) δ: 155.79, 152.23, 149.44, 141.46, 118.55, 59.17, 45.61. MS (GT, FAB+): 136 (B+1H)+, 180 (M+1H)+, 202 (M+Na)+.

후처리

  1. filtrationThe mixture was then filtered
  2. customto remove insoluble materiel
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was triturated with EtOAc
  5. filtrationthen filtered
  6. customto give a white solid, which
  7. stirringThe reaction mixture was stirred for 14 h at room temperature
  8. custommethanol was removed under reduced pressure
  9. customRecrystallization from EtOH afforded compound 2 (5.87 g, 85%)
  10. custommp 236° C. (Lit. 238-239° C.)

출처 및 근거

ORD 기록
ord-91dc02665b9c4ab98a90a2ab37b24071
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884011B2

연결된 노트

불러오는 중…