4-Cyanobenzaldehyde → HCID 69534073, compound

HRID 2268373Notes

Reaction equation

HRID 2268373 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+].[C:51]([C:53]1[CH:60]=[CH:59][C:56]([CH:57]=O)=[CH:55][CH:54]=1)#[N:52]>>[OH:17][C@@H:16]1[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13][C@H:12]1[N:9]1[CH:8]=[N:7][C:6]2[C:10]1=[N:11][C:3]([CH2:2][NH:1][CH2:57][C:56]1[CH:59]=[CH:60][C:53]([C:51]#[N:52])=[CH:54][CH:55]=1)=[N:4][C:5]=2[NH:22][CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 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 69534073HCID 69534073, compoundYield 42.3%

Procedure

The title compound was prepared by a similar method to example 5 from (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (400 mg, 0.82 mmol), sodium triacetoxyborohydride (260 mg, 1.22 mmol) and 4-cyanobenzaldehyde (120 mg, 0.9 mmol) The product was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:ammonia (92:7:1) gradually increasing polarity to dichloromethane:methanol:ammonia (90:10:1), which gave the title compound (210 mg) as a foam. MS: 606 (MH+).

Workup

  1. customwas purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:ammonia (92:7:1)
  2. temperaturegradually increasing polarity to dichloromethane:methanol:ammonia (90:10:1), which

Sources & evidence

ORD record
ord-9df229c03826494fbce898ab1e464c15
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

Loading…