Triethylamine → (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(methoxyamino)-2-(phenylethynyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

HRID 895102

반응식

HRID 895102 반응식
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][C:19](I)=[N:20][C:21]=3[NH:25][O:26][CH3:27])[C@H:13]([OH:29])[C@@H:12]1[OH:30].C(N(CC)CC)C>CN(C)C=O.[Cu]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>[OH:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][C:19]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:20][C:21]=3[NH:25][O:26][CH3:27])[C@H:13]([OH:29])[C@@H:12]1[OH:30]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 16115751(4S,2R,3R,5R)-5-(hydroxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolane-3,4-diol

생성물 1

HCID 10046345(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(methoxyamino)-2-(phenylethynyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

CuI (0.35 mg, 0.002 mmol) and phenylacetylene (2.1 mmol) were added to a solution of (4S,2R,3R,5R)-5-(hydroxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolane-3,4-diol (0.35 mmol), a compound of formula (5), in dry N,N-dimethylformamide (6 mL) and triethylamine (1.4 mL) under an atmosphere of nitrogen in the presence of bis(triphenylphosphine)palladium dichloride (5 mg, 0.007 mmol). The reaction mixture was stirred at room temperature for 5 hours. After evaporation under reduced pressure the residual oil was purified by silica gel column chromatography, eluting with chloroform/methanol 90/10. After evaporation in vacuo, the residual oil was purified by silica gel column chromatography, eluting with the suitable mixture of solvents, to provide (4S,2R,3R,5R)-5-(hydroxymethyl)-2-[6-(methoxyamino)-2-(2-phenylethynyl)purin-9-yl]oxolane-3,4-diol, a compound of Formula I (mp 175-177° C.).

후처리

  1. customAfter evaporation under reduced pressure the residual oil
  2. customwas purified by silica gel column chromatography
  3. washeluting with chloroform/methanol 90/10
  4. customAfter evaporation in vacuo
  5. customthe residual oil was purified by silica gel column chromatography
  6. washeluting with the suitable mixture of solvents

출처 및 근거

ORD 기록
ord-716de53f06884d07ad44a733f68eff90
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06914053B2

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