4-Chlorobenzaldehyde → HCID 59975336, compound

HRID 2268363Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)=[C:5]([NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:51][C:52]1[CH:59]=[CH:58][C:55]([CH:56]=O)=[CH:54][CH:53]=1>>[Cl:51][C:52]1[CH:59]=[CH:58][C:55]([CH2:56][NH:1][CH2:2][C:3]2[N:11]=[C:10]3[C:6]([N:7]=[CH:8][N:9]3[C@H:12]3[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]3)=[C:5]([NH:22][CH2:23][CH:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:4]=2)=[CH:54][CH:53]=1

Participants

Reactant 3

HCID 77264-Chlorobenzaldehyde

HCID 5049666Sodium triacetoxyborohydride

HCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 59975336HCID 59975336, compoundYield 21.5%

Procedure

The title compound was prepared by a similar method to example 5 using (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (200 mg, 0.4 mmol), sodium triacetoxyborohydride (152 mg, 0.72 mmol) and 4-chlorobenzaldehyde (75 mg, 0.53 mmol). The product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (98:2) gradually increasing polarity to dichloromethane:methanol (90:10), which gave the title compound (53 mg) as a foam. MS: 615 (MH+).

Workup

customThe product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (98:2)
temperaturegradually increasing polarity to dichloromethane:methanol (90:10), which

Sources & evidence

ORD record: ord-2928481d82ff44f7ba1c82ea5fe500a2
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326359B1

Reaction notes

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