Ammonia → HCID 54154356, compound

HRID 1647188Notes

Reaction equation

[CH3:1][N:2]([CH3:4])[NH2:3].C([O:8][C@@H:9]1[C@H:13]([O:14]C(=O)C)[C@@H:12]([CH2:18][O:19]C(=O)C)[O:11][C@H:10]1[N:23]1[CH:31]=[N:30][C:29]2[C:24]1=[N:25][C:26]([NH2:33])=[N:27][C:28]=2Cl)(=O)C.N>>[NH2:33][C:26]1[N:27]=[C:28]([NH:3][N:2]([CH3:4])[CH3:1])[C:29]2[N:30]=[CH:31][N:23]([C:24]=2[N:25]=1)[C@@H:10]1[O:11][C@H:12]([CH2:18][OH:19])[C@@H:13]([OH:14])[C@H:9]1[OH:8]

Participants

Reactant 3

HCID 222Ammonia

HCID 59761,1-Dimethylhydrazine

HCID 10788628(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Product 1

HCID 54154356HCID 54154356, compoundYield 45%

Procedure

The title compound was prepared according to method A as described in example 4 by reacting 1,1-dimethylhydrazine (0.79 g, 13.1 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-chloro-9H-purine (4.0 g, 9.35 mmol) and debenzoylating the purified product using methanolic ammonia to provide the title 2-amino-N-(dimethylamino)adenosine (after column chromatography) as an amorphous foam (0.56 g, 45%), 1H NMR (DMSO-d6)γ 2.54 (6H, s, 2×--CH3), 3.50-3.57 (1H, m, H-5'b), 3.61-3.68 (1H, m, H-5'b), 3.93 (1H, q, H-4'), 4.12 (1H, q, H-3'), 4.51 (1H, q, H-2'), 5.12, 5.38 (2H, 2d, 2'- and 3'-OH), 5.42 (1H, t, 5'-OH), 5.76 (1H, d, H-1'), 5.95 (2H, s, --NH2), 7.93 (1H, s, H-8), 8.20 (1H, s, N-H).

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-d6e6d77516254fdeb404ff2299ba1d55
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05430027

Reaction notes

Loading…