Ammonia → HCID 53887934, compound

HRID 1647189Notes

Reaction equation

HRID 1647189 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:3].C([O:21][C@@H:22]1[C@H:26]([O:27]C(=O)C2C=CC=CC=2)[C@@H:25]([CH2:36][O:37]C(=O)C2C=CC=CC=2)[O:24][C@H:23]1[N:46]1[CH:54]=[N:53][C:52]2[C:47]1=[N:48][C:49]([Cl:56])=[N:50][C:51]=2Cl)(=O)C1C=CC=CC=1.C(N(CC)CC)C.N>O1CCOCC1>[Cl:56][C:49]1[N:50]=[C:51]([NH:3][N:2]([CH3:1])[CH2:4][CH2:5][O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:52]2[N:53]=[CH:54][N:46]([C:47]=2[N:48]=1)[C@@H:23]1[O:24][C@H:25]([CH2:36][OH:37])[C@@H:26]([OH:27])[C@H:22]1[OH:21]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 19926394HCID 19926394, compound

Product 1

HCID 53887934HCID 53887934, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared according to method A by reacting 1-methyl-1-(2-phenoxyethyl)hydrazine (prepared by the general method described in example 1) (0.80 g, 4 mmol) and 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.53 g, 4 mmol) and triethylamine (1.11 ml, 8 mmol) in dioxan (25 ml), followed by debenzoylation of the purified product using methanolic ammonia to provide the title 2-chloro-N-(N-methyl-N-(2-phenoxyethyl)amino)adenosine (0.84 g, 47%) (after column chromatography) obtained as a solid, mp 166°-8° C., 1H NMR (DMSO-d6)γ 2.70 (3H, s, --CH3), 3.22 (2H, br t, --CH2 --), 3.51-3.58 (1H, m, H-5'a), 3.62-3.69 (1H, m, H-5'a), 3.95 (1H, q, H-4'), 4.05-4.15 (3H, m, --CH2 -- and H-3' ), 4.50 (1H, q, H-2'), 5.06 (1H, t, 5'-OH), 5.21, 5.49 (2H, 2d, 2'- and 3--OH), 5.81 (1H, H-1'), 6.79-7.25 (5H, m, Ar-H), 8.41 (1H, s, H-8), 9.41 (1H, br s, N-H).

Workup

  1. customThe title compound was prepared
  2. customprepared by the general method

Sources & evidence

ORD record
ord-ff6d42a9f78f49f2a3f50988ab4906b5
Source dataset
uspto-grants-1995_07
Patent number
US05430027

Reaction notes

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