Tetrahydrofuran → (2R,3R,4S,5R)-2-(6-[(2,2-Diphenylethyl)amino]-2-{[2-(1-piperidinyl)ethoxy]methyl}-9H-purin-9-yl)-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268374Notes

Reaction equation

[Si]([O:8][C@@H:9]1[C@H:13]([O:14][Si](C(C)(C)C)(C)C)[C@@H:12]([CH2:22][O:23][CH3:24])[O:11][C@H:10]1[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][C:28]([CH2:49][O:50][CH2:51][CH2:52][N:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1)=[N:29][C:30]=2[NH:34][CH2:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[C:43]1([CH:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:35][NH:34][C:30]2[N:29]=[C:28]([CH2:49][O:50][CH2:51][CH2:52][N:53]3[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]3)[N:27]=[C:26]3[C:31]=2[N:32]=[CH:33][N:25]3[C@H:10]2[C@H:9]([OH:8])[C@H:13]([OH:14])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11]2)[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

HCID 69534113N-(9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[2-(1-piperidinyl)ethoxy]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine

Product 1

HCID 59975304(2R,3R,4S,5R)-2-(6-[(2,2-Diphenylethyl)amino]-2-{[2-(1-piperidinyl)ethoxy]methyl}-9H-purin-9-yl)-5-(methoxymethyl)tetrahydro-3,4-furandiolYield 30.4%

Procedure

The title compound was prepared by a similar method to example 38 using N-(9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[2-(1-piperidinyl)ethoxy]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine (100 mg, 0.12 mmol) (preparation 29), and a 1M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.5 ml, 0.5 mmol). The compound was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.5) to give the title compound (22 mg) as a gum. MS: 604 (MH+).

Workup

customThe compound was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.5)

Sources & evidence

ORD record: ord-c04ecf9cf9a746be9b321560be48c284
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326359B1

Reaction notes

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