Ammonia → 4-(2-Amino-1-hexen-1-yl)-1-beta-D-ribofuranosyl-pyrimidin-2-one

HRID 840610Notes

Reaction equation

HRID 840610 reaction equation
[C:1]([C:7]1[CH:12]=[CH:11][N:10]([C@@H:13]2[O:35][C@H:34]([CH2:36][O:37]C(=O)C3C=CC=CC=3)[C@@H:24]([O:25]C(=O)C3C=CC=CC=3)[C@H:14]2[O:15]C(=O)C2C=CC=CC=2)[C:9](=[O:46])[N:8]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH3:47]>>[NH2:47][C:2]([CH2:3][CH2:4][CH2:5][CH3:6])=[CH:1][C:7]1[CH:12]=[CH:11][N:10]([C@@H:13]2[O:35][C@H:34]([CH2:36][OH:37])[C@@H:24]([OH:25])[C@H:14]2[OH:15])[C:9](=[O:46])[N:8]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 103941024-(1-Hexyn-1-yl)-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

Product 1

HCID 701689454-(2-Amino-1-hexen-1-yl)-1-beta-D-ribofuranosyl-pyrimidin-2-one

Procedure

A solution of 14a (1.2 g, 1.9 mmol) in methanolic ammonia (saturated at −20° C.) was stirred in a pressure bottle for 18 hr. Evaporation of the solvents and flash chromatography of the residue using ethyl acetate/methanol (4:1) gave 17a as a light yellow solid, 0.47 g (77%). 1H-NMR (DMSO-d6): δ10.2 and 7.7 (2 bs, 2H, NH2); 7.83 (d, 1H, H-6, J6,5=6.9 Hz); 5.78 (s, 1H, H-1′); 4.72 (s, 1H, vinylic); 2.17, 1.50, 1.30 and 0.90 (4 m, 9H, n-butyl).

Workup

  1. customEvaporation of the solvents and flash chromatography of the residue

Sources & evidence

ORD record
ord-18eba2afb7f9467ba58df8c2360a89e8
Source dataset
uspto-grants-2002_04
Patent number
US06369040B1

Reaction notes

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