Hydrochloric Acid → 2-Amino-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-5-methyl-7h-pyrrolo[2,3-d]pyrimidine-4(3h)-one

HRID 2212925Notes

Reaction equation

HRID 2212925 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:28][C@H:27]([CH2:29][O:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=4[Cl:39])[C@@H:16]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=4[Cl:26])[C@@:13]3([CH3:40])[O:14][CH3:15])[C:6]=2[N:7]=1.Cl.[O:43]1CCOCC1>[OH-].[Na+]>[NH2:1][C:2]1[NH:3][C:4](=[O:43])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:28][C@H:27]([CH2:29][O:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=4[Cl:39])[C@@H:16]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=4[Cl:26])[C@@:13]3([CH3:40])[O:14][CH3:15])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 235183222-Amino-4-chloro-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-5-methyl-7h-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 1363907652-Amino-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-5-methyl-7h-pyrrolo[2,3-d]pyrimidine-4(3h)-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of the product from Step B (200 mg, 0.3 mmol) in 1,4-dioxane (15 mL) and aqueous NaOH (2N, 15 mL) in a pressure bottle was heated overnight at 135° C. The mixture was then cooled to 0° C., neutralized with 2N aqueous HCl and evaporated to dryness. The crude product was suspended in MeOH, filtered, and the solid thoroughly washed with MeOH. The combined filtrate was concentrated, and the residue purified on a silica gel column (5×5 cm) using CH2Cl2/MeOH (40/1, 30/1 and 20/1) as eluent to give the desired compound (150 mg) as a colorless foam.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. customevaporated to dryness
  3. filtrationfiltered
  4. washthe solid thoroughly washed with MeOH
  5. concentrationThe combined filtrate was concentrated
  6. customthe residue purified on a silica gel column (5×5 cm)

Sources & evidence

ORD record
ord-592cb240cf7449c98d30d9a52bba3d09
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

Loading…