Tetrahydrofuran → HCID 59975337, compound

HRID 2268382Notes

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][CH2:50][NH:51][CH2:52][CH2:53][O:54][CH3:55])=[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:37]1([CH:36]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:35][NH:34][C:30]2[N:29]=[C:28]([CH2:49][CH2:50][NH:51][CH2:52][CH2:53][O:54][CH3:55])[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:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

HCID 69534117HCID 69534117, compound

Product 1

HCID 59975337HCID 59975337, compoundYield 46.8%

Procedure

The title compound was prepared by a similar method to example 38 using N-(2-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}ethyl)-N-(2-methoxyethyl)amine (150 mg, 0.19 mmol) (preparation 34) and a 1 molar 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 gradient of dichloromethane:methanol:ammonia (94:6:0.6) increasing in polarity to (90:10:1) to give the title compound (50 mg) as a foam. MS: 563 (MH+).

Workup

customThe compound was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (94:6:0.6)
temperatureincreasing in polarity to (90:10:1)

Sources & evidence

ORD record: ord-2b1c9e4d9a0a453aabd8030a642a53cd
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326359B1

Reaction notes

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