Ammonia → HCID 135427937, compound

HRID 420878Notes

Reaction equation

HRID 420878 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:46])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:34][C@H:33]([CH2:35][O:36]C(=O)C4C=CC=CC=4)[C@@H:23]([O:24]C(=O)C4C=CC=CC=4)[C@@:13]3([CH3:45])[O:14]C(=O)C3C=CC=CC=3)[C:6]=2[N:7]=1.N>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:46])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:23]([OH:24])[C@@:13]3([CH3:45])[OH:14])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 1361316075-Amino-3-(2',3',5'-tri-O-benzoyl-2'-C-methyl-beta-D-ribofuranosyl)-3H,6H-thiazolo[4,5-d]pyrimidine-2,7-dione

Product 1

HCID 135427937HCID 135427937, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of nucleoside triester 119 (209 mg, 0.325 mmol) and MeOH (10 mL) saturated with NH3 (g) at −30° C. was stirred in a sealed tube for 48 h. The mixture was warmed to rt, depressurized, concentrated then submitted to HPLC purification (MeCN—H2O), affording 36 mg (34%) of the title compound as a white solid after lyophilization: 1H (400 MHz, DMSO-d6) δ 11.18 (s, 1H), 6.92 (br s, 2H), 5.95 (s, 1H), 5.18-5.28 (br m, 1H), 4.75 (br s, 1H), 4.53 (dd, J=11.3, 5.46, 1H), 3.95 (br s, 1H), 3.73-3.78 (m, 1H), 3.29 (br s, 2H), 1.04 (s, 3H); [M+H]+ m/z 331.

Workup

  1. concentrationconcentrated
  2. customthen submitted to HPLC purification (MeCN—H2O)

Sources & evidence

ORD record
ord-9180226a73ab40279884e3ad9860244d
Source dataset
uspto-grants-2012_01
Patent number
US08097718B2

Reaction notes

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