Dichloromethane → HCID 22877230, compound

HRID 1379647Notes

Reaction equation

HRID 1379647 reaction equation
[CH3:1][CH:2]([CH3:13])[C@@H:3]([NH2:12])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([O:22][C@@H:23]1[C@H:27]([O:28]C(=O)C2C=CC=CC=2)[C@@H:26]([CH2:37][O:38]C(=O)C2C=CC=CC=2)[O:25][C@H:24]1[N:47]1[CH:55]=[N:54][C:53]2[C:48]1=[N:49][C:50]([Cl:57])=[N:51][C:52]=2Cl)(=O)C1C=CC=CC=1.C(N(CC)CC)C.ClCCl>O1CCOCC1>[Cl:57][C:50]1[N:51]=[C:52]([NH:12][C@H:3]([CH:2]([CH3:13])[CH3:1])[CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:53]2[N:54]=[CH:55][N:47]([C:48]=2[N:49]=1)[C@@H:24]1[O:25][C@H:26]([CH2:37][OH:38])[C@@H:27]([OH:28])[C@H:23]1[OH:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 54555958HCID 54555958, compound

Product 1

HCID 22877230HCID 22877230, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-3-methyl-1-phenoxy-2-butylamine (0.6 g, 2.8 mmol) was reacted with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.4 g, 2.2 mmol) in dioxan (20 ml) in the presence of triethylamine (0.5 g, 5.0 mmol). The reaction mixture was stirred at room temperature for 40 h before being filtered and evaporated. The product (after purification by flash chromatography) was debenzoylated with methanolic ammonia to provide the product (after column chromatography) as a foam which solidified on coevaporation with dichloromethane. 2-Chloro- N-[(R)-3-methyl-1-phenoxy2-butyl]adenosine (0.46 g, 44%) was obtained as a white solid, mp 95°-100° C., 1H NMR (DMSO-d6)δ 0.95, 0.98 (6H, 2d, 2×--CH3), 2.10 (1H, m, --C H(CH3)2), 3.53-3.60 (1H, m, H-5'a), 3.63-3.71 (1H, m, H-5'b), 3.95 (1H, q, H-4), 4.07-4.23 (3H, m, H-3' and --CH2 --), 4.96 (1H, m, --C--H), 4.56 (1H, q, H-2'), 5.08 (1H, t, 5'-OH), 5.23, 5.49 (2H, 2d, 2' and 3'-OH), 5.84 (1H, d, H-1'), 6.87-6.97 (3H, m, Ar--H), 7.24-7.31 (2H, dd, Ar--H), 8.36 (1H, d, --N--H), 8.40 (1H, s, H-8).

Workup

  1. filtrationbefore being filtered
  2. customevaporated
  3. customThe product (after purification by flash chromatography)
  4. customto provide the product (after column chromatography) as a foam which

Sources & evidence

ORD record
ord-033c2bac2ecb49cc8bd4f1d70d8ad986
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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