Triethylamine → (4S,2R,3R,5R)-2-{6-amino-2-[3-(2-phenylphenoxy)prop-1-ynyl]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol

HRID 567669

반응식

HRID 567669 반응식
[NH2:1][C:2]1[N:10]=[C:9](I)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:12]1[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][OH:20])[O:13]1.[CH2:21]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:22]#[CH:23].C(N([CH2:36][CH3:37])CC)C>CN(C)C=O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:10]=[C:9]([C:23]#[C:22][CH2:21][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:37]2[CH:36]=[CH:16][CH:15]=[CH:14][CH:19]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:12]1[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][OH:20])[O:13]1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 83613(Prop-2-ynyloxy)benzeneHCID 1696622-Iodoadenosine2회

생성물 1

HCID 9804898(4S,2R,3R,5R)-2-{6-amino-2-[3-(2-phenylphenoxy)prop-1-ynyl]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol수율 38.1%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of (4S,2R,3R,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol (compound 1) (50 mg, 0.126 mmol) and prop-2-ynyloxybenzene (22 δ, 0.1605 mmol) in N,N-dimethylformamide (1 ml) and triethylamine (21 δ, 16.065 mmol) at 23° C. was added copper iodide (5 mg, 0.026 mmol) and dichlorobis(triphenylphosphine)palladium(II) (22 mg, 0.031 mmol) catalyst. After being stirred in a sealed reacti-vial at 80 C for 6 hours, the reaction was concentrated in vacuo, the residue purified by preparatory thin layer chromatography (methylene chloride:methanol 9:1) to afford compound 10 (9.6 mg, 0.024 mmol) in 20% yield. 1H NMR(CDCl3:CD3OD 9:1) δ 3.02-3.04 (m, 1H), 3.07 (s, 1H), 3.55, 3.74 (dd, 2H), 4.02 (s, 1H), 4.11-4.13 (m, 1H), 4.48-4.52 (m, 1H), 4.72 (s, 2H), 5.65 (d, 1H), 6.75-6.82 (m, 3H), 7.08-7.12 (m, 2H), 7.94 (s, 1H).

후처리

  1. concentrationthe reaction was concentrated in vacuo
  2. customthe residue purified by preparatory thin layer chromatography (methylene chloride:methanol 9:1)

출처 및 근거

ORD 기록
ord-0509b07fb38a469eb0d4cf0dd4648434
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180615B2

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