Tetrahydrofuran → (2R,3R,4S,5R)-2-{2-{2-[(1-Benzhydryl-3-azetidinyl)amino]ethyl}-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268390Notes

Reaction equation

[CH:1]([N:14]1[CH2:17][CH:16]([NH:18][CH2:19][CH2:20][C:21]2[N:29]=[C:28]3[C:24]([N:25]=[CH:26][N:27]3[C@H:30]3[C@H:34]([O:35][Si](C(C)(C)C)(C)C)[C@H:33]([O:43][Si](C(C)(C)C)(C)C)[C@@H:32]([CH2:51][O:52][CH3:53])[O:31]3)=[C:23]([NH:54][CH2:55][CH:56]([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[N:22]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[CH:1]([N:14]1[CH2:15][CH:16]([NH:18][CH2:19][CH2:20][C:21]2[N:29]=[C:28]3[C:24]([N:25]=[CH:26][N:27]3[C@H:30]3[C@H:34]([OH:35])[C@H:33]([OH:43])[C@@H:32]([CH2:51][O:52][CH3:53])[O:31]3)=[C:23]([NH:54][CH2:55][CH:56]([C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[N:22]=2)[CH2:17]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

HCID 867576422-{2-[(1-benzhydryl-3-azetidinyl)amino]ethyl}-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-N-(2,2-diphenylethyl)-9H-purin-6-amine

Product 1

HCID 59975332(2R,3R,4S,5R)-2-{2-{2-[(1-Benzhydryl-3-azetidinyl)amino]ethyl}-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiolYield 68.9%

Procedure

The title compound was prepared by a similar method to example 38 using 2-{2-[(1-benzhydryl-3-azetidinyl)amino]ethyl}-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-N-(2,2-diphenylethyl)-9H-purin-6-amine (130 mg, 0.14 mmol) (preparation 38) and a 1 molar solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.4 ml, 0.4 mmol). The compound was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (95:5:0.5) increasing in polarity to (90:10:1) to give the title compound (70 mg) as a foam. MS: 726 (MH+).

Workup

customThe compound was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (95:5:0.5)
temperatureincreasing in polarity to (90:10:1)

Sources & evidence

ORD record: ord-d34cee5bd85743eba46845bbd6b38b4a
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326359B1

Reaction notes

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