2-Iodoadenosine → 2-(Trifluoromethyl)adenosine

HRID 2050602노트

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HRID 2050602 반응식
[Br-].[F:2][C:3]([Zn+])([F:5])[F:4].I[C:8]1[N:9]=[C:10]([NH2:26])[C:11]2[N:12]=[CH:13][N:14]([C:24]=2[N:25]=1)[C@@H:15]1[O:23][C@H:20]([CH2:21][OH:22])[C@@H:18]([OH:19])[C@H:16]1[OH:17]>CN(C=O)C.CN(P(N(C)C)(N(C)C)=O)C.[Cu](Br)Br>[F:2][C:3]([F:5])([F:4])[C:8]1[N:9]=[C:10]([NH2:26])[C:11]2[N:12]=[CH:13][N:14]([C:24]=2[N:25]=1)[C@@H:15]1[O:23][C@H:20]([CH2:21][OH:22])[C@@H:18]([OH:19])[C@H:16]1[OH:17]

참가 물질

6

반응물 2

HCID 1696622-IodoadenosineHCID 178506396HCID 178506396, 화합물

생성물 1

HCID 144303552-(Trifluoromethyl)adenosine수율 63%

시약·촉매·용매 3

HCID 24611Copper bromide (CuBr2)촉매HCID 6228Dimethylformamide용매HCID 12679Hexamethylphosphoramide용매

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온도
70 °C

실험 절차

A solution of trifluoromethylzinc bromide (1.308 g, 6.10 mmol) in DMF (25 mL) and HMPA (10 mL) was added to copper bromide (0.438 g, 3.05 mmol) and the resulting mixture was stirred for 30 min. 2-Iodoadenosine (0.800 g, 2.03 mmol) was added and the solution was warmed at 70° C. for 4 h. The solvents were evaporated and the residue was purified on silica gel with 10% methanol/chloroform to give 2-trifluoromethyladenosine in 63% yield. 2-Trifluoromethyladenosine was converted to IV by using in sequence the following procedures: Procedure A (58% yield), Procedure B (84% yield), Procedure C (51% yield), Procedure D (73% yield), Procedure E (75% yield), and Procedure F (53% yield): mp 173°-175° C.; 13NMR (Me2SO-d6) δ25.7, 31.8, 62.8, 82.1, 84.5, 119.8, 141.1, 148.3, 156.2; 1H NMR (Me2SO-d6) δ2.10 (m, 2 H), 2.40 (m, 2H), 3.51 (m, 2H), 4.13 (m, 1H), 4.88 (m, 1H), 6.25 (m, 1H), 7.85 (br.s, 2H), 8.54 (s, 1H); UV (H2O) λmax 259.5 nm (λ11300); FAB HRMS obsd (M+ +H) 304.0996, calcd for C11H12F3N5O2 304.1021.

후처리

  1. customThe solvents were evaporated
  2. customthe residue was purified on silica gel with 10% methanol/chloroform

출처 및 근거

ORD 기록
ord-cd6396301ca64dd5967bc19a27395ba4
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05013829

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