1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 86658528, compound

HRID 1043400Notes

Reaction equation

HRID 1043400 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@:12]2([F:20])[CH3:19])=[C:4]([O:21][CH3:22])[N:3]=1.[C:23](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:32]1[CH:39]=[CH:38][C:35]([O:36][CH3:37])=[CH:34][CH:33]=1)[C:24]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH3:29][O:28][C:27]1[CH:30]=[CH:31][C:24]([C:23]([C:32]2[CH:39]=[CH:38][C:35]([O:36][CH3:37])=[CH:34][CH:33]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:17][CH2:16][C@@H:14]2[C@@H:13]([OH:18])[C@:12]([F:20])([CH3:19])[C@H:11]([N:8]3[CH:7]=[N:6][C:5]4[C:9]3=[N:10][C:2]([NH:1][C:23]([C:24]3[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[CH:26][CH:25]=3)([C:32]3[CH:39]=[CH:38][C:35]([O:36][CH3:37])=[CH:34][CH:33]=3)[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[N:3][C:4]=4[O:21][CH3:22])[O:15]2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 46844020HCID 46844020, compound

Product 1

HCID 86658528HCID 86658528, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2R,3R,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol (2, 4 g, 12.8 mmol) in anhydrous pyridine (100 mL) cooled at 0° C. was added DMT-Cl portion-wise under nitrogen. The brown solution was stirred at ambient temperature for 24 hours. The mixture was concentrated under reduced pressure to remove most of solvent and sat. NaHCO3 (20 mL) was added. The mixture was diluted with water (150 mL) and EtOAc (120 mL). The organic layer was separated and washed with water (5×120 mL), brine and dried over Na2SO4. After removal of solvent, the residue was purified via column chromatography (20% EA in hexanes to 80% EA in hexanes) to afford 11.6 g of product, 3, as a white foam solid (quantitative yield). 1H-NMR (DMSO-d6): δ 7.94 (s, 1H), 7.39-7.37 (m, 3 H), 7.26-7.14 (m, 17H), 6.84-6.80 (m, 8H), 5.58 (s, 1H), 4.04 (br, 1H), 3.71-3.70 (m, 14H), 3.68 (m, 1H), 3.48 (br, 2H), 3.20 (d, 1H), 0.88 (br, 3H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove most of solvent and sat. NaHCO3 (20 mL)
  3. additionwas added
  4. additionThe mixture was diluted with water (150 mL) and EtOAc (120 mL)
  5. customThe organic layer was separated
  6. washwashed with water (5×120 mL), brine
  7. dry with materialdried over Na2SO4
  8. customAfter removal of solvent
  9. customthe residue was purified via column chromatography (20% EA in hexanes to 80% EA in hexanes)

Sources & evidence

ORD record
ord-0f0d5836cefa478a8a2529593d346447
Source dataset
uspto-grants-2013_10
Patent number
US08563530B2

Reaction notes

Loading…