Tetrahydrofuran → HCID 59975284, compound

HRID 2268396Notes

Reaction equation

[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[C@H:20]2[C@H:24]([O:25][Si](C(C)(C)C)(C)C)[C@H:23]([O:33][Si](C(C)(C)C)(C)C)[C@@H:22]([CH2:41][O:42][CH3:43])[O:21]2)=[C:13]([NH:44][CH2:45][CH:46]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[C@H:20]2[C@H:24]([OH:25])[C@H:23]([OH:33])[C@@H:22]([CH2:41][O:42][CH3:43])[O:21]2)=[C:13]([NH:44][CH2:45][CH:46]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

HCID 69534115N-benzyl-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)amine

Product 1

HCID 59975284HCID 59975284, compoundYield 61.9%

Procedure

The title compound was prepared by a similar method to example 38 using N-benzyl-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)amine (360 mg, 0.44 mmol) (preparation 39) and a 1 molar solution of tetrabutylammonium fluoride in tetrahydrofuran (0.92 ml, 0.92 mmol). The product was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (93:7) increasing in polarity to dichloromethane:methanol:ammonia (90:10:1) to give the title compound (162 mg) as a foam. MS: 596 (MH+).

Workup

customThe product was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (93:7)
temperatureincreasing in polarity to dichloromethane:methanol:ammonia (90:10:1)

Sources & evidence

ORD record: ord-504b97c0ee83433caf04d00d2608afc1
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326359B1

Reaction notes

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