Triethylamine → HCID 22877223, compound

HRID 1379639Notes

Reaction equation

HRID 1379639 reaction equation
[C:1]1([S:7][CH2:8][C@H:9]([NH2:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:20][C@@H:21]1[C@H:25]([O:26]C(=O)C2C=CC=CC=2)[C@@H:24]([CH2:35][O:36]C(=O)C2C=CC=CC=2)[O:23][C@H:22]1[N:45]1[CH:53]=[N:52][C:51]2[C:46]1=[N:47][C:48]([Cl:55])=[N:49][C:50]=2Cl)(=O)C1C=CC=CC=1.C(N(CC)CC)C>O1CCOCC1>[Cl:55][C:48]1[N:49]=[C:50]([NH:11][C@H:9]([CH3:10])[CH2:8][S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:51]2[N:52]=[CH:53][N:45]([C:46]=2[N:47]=1)[C@@H:22]1[O:23][C@H:24]([CH2:35][OH:36])[C@@H:25]([OH:26])[C@H:21]1[OH:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 13628021HCID 13628021, compound

Product 1

HCID 22877223HCID 22877223, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-1-Phenylthio-2-propylamine (0.4 g, 1.96 mmol) was reacted with 9-(2,3.5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.2 g, 1.9 mmol) in dioxan (15 ml) in the presence of triethylamine (0.4 g, 4 mmol). The reaction mixture was stirred at room temperature for 72 h, heated at 50° C. for 24 h, cooled, filtered and evaporated. The product (after purification by flash chromatography) was debenzoylated with methanolic ammonia to provide the title 2-chloro- N-[(R)-1-phenylthio-2-propyl]adenosine (after column chromatography) as a foam (0.47 g, 52%), 1H NMR (DMSO-d6)δ 1.34 (3H, d, --CH3), 3.01 (1H, dd, --C--H), 3.52-3.60 (1H, m, H-5'a), 3.62-3.72 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.13 (1H, m, H-3'), 4.30-4.45 (1H, m, --C--H), 4.53 (1H, m, H-2'), 5.09, 5.22, 5.50 (3H, 3 br, 2', 3' and 5'-OH), 5.84 (1H, d, H-1'), 7.19 (1H, t, Ar--H), 7.30 (2H, t, Ar--H), 7.45 (2H, d, Ar--H), 8.29-8.45 (2H, s & m, H-8 and N--H).

Workup

  1. temperatureheated at 50° C. for 24 h
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated
  5. customThe product (after purification by flash chromatography)

Sources & evidence

ORD record
ord-4ee50013b4b34339b669a767ff854f44
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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