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

HRID 895102

Reaction equation

HRID 895102 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-716de53f06884d07ad44a733f68eff90
Source dataset
uspto-grants-2005_07
Patent number
US06914053B2

Linked notes

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