4-Isopropoxybenzaldehyde → HCID 59975299, compound

HRID 2268365Notes

Reaction equation

HRID 2268365 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+].[CH:51]([O:54][C:55]1[CH:62]=[CH:61][C:58]([CH:59]=O)=[CH:57][CH:56]=1)([CH3:53])[CH3:52]>O1CCCC1>[C:25]1([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:23][NH:22][C:5]2[N:4]=[C:3]([CH2:2][NH:1][CH2:59][C:58]3[CH:61]=[CH:62][C:55]([O:54][CH:51]([CH3:53])[CH3:52])=[CH:56][CH:57]=3)[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[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)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 2500774-IsopropoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 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 59975299HCID 59975299, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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) (225 mg, 0.46 mmol), sodium triacetoxyborohydnde (212 mg, 1.0 mmol) and 4-isopropoxybenzaldehyde (84 mg, 0.51 mmol) in tetrahydrofuran (15 ml). The product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.5). This gave the title compound (53 mg) as a foam. MS: 639 (MH+).

Workup

  1. customThe product 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-d7d98927d73c491cbac2ff8ffa023f73
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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