1-Phenoxy-2-propanamine → HCID 22877232, compound

HRID 1379633Notes

Reaction equation

HRID 1379633 reaction equation
[O:1]([CH2:8][CH:9]([NH2:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:12]1[N:17]=[C:16](Cl)[C:15]2[N:19]=[CH:20][N:21]([C@@H:22]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:24]([OH:29])[C@H:23]3[OH:30])[C:14]=2[N:13]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[O:1]([CH2:8][CH:9]([NH:11][C:16]1[C:15]2[N:19]=[CH:20][N:21]([C:14]=2[N:13]=[CH:12][N:17]=1)[C@@H:22]1[O:26][C@H:25]([CH2:27][OH:28])[C@@H:24]([OH:29])[C@H:23]1[OH:30])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 370871-Phenoxy-2-propanamineHCID 81531DiisopropylethylamineHCID 930036-Chloropurine riboside

Product 1

HCID 22877232HCID 22877232, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Phenoxy-2-propylamine (0.33 g, 2.18 mmol) was reacted with 6-chloropurine riboside (i.e. 9-β-D-ribofuranosyl-9H-purine)(0.5 g, 1.7 mmol) in dioxan (30 ml) in the presence of diisopropylethylamine (0.28 g, 2.2 mmol). The reaction mixture was heated at reflux for 5 h, cooled and evaporated. The residue was purified by flash chromatography on silica gel to provide the N-(1-Phenoxy-2-propyl)adenosine (a mixture of diastereoisomers) as a foam (0.06 g, 7%), 1H NMR (DMSO-d6)δ 1.32 (3H, d, --CH3), 3.52-3.60 (1H, m, H-5'a), 3.64-3.71 (1H, m, H-5'b), 3.93-3.99 and 4.12-4.20 (4H, 2m, m, H-4', H-3' and --CH2 --), 4.62 (1H, q, H-2'), 4.68-4.82 (1H, m, --C HCH3), 5.40 (1H, t, 5'-0H), 5.20, 5.45 (2H, 2d, 2'- and 3'-OH), 5.90 (1H, d, H-1'), 6.88-6.98 (3H, m, Ar--H), 7.23-7.31 (2H, t, Ar--H), 7.85, 8.21, 8.38 (3H, 3s, H-2, H-8 and N--H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. temperaturecooled
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8553f1fd8f664843b36d4a72f3c68c9b
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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