HCID 10268360, compound → HCID 67142878, compound
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:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@H:13]3[O:14][CH3:15])[C:6]=2[N:7]=1.[CH3:23][O-:24].[Na+].CO>>[NH2:1][C:2]1[N:3]=[C:4]([O:24][CH3:23])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@H:13]3[O:14][CH3:15])[C:6]=2[N:7]=1Participants
Procedure
A solution of the compound from Step A (50 mg, 0.15 mmol) in 0.5M NaOMe/MeOH (4 mL) was stirred at reflux temperature for 1.5 h. The mixture was cooled, mixed with silica gel and evaporated to dryness. The silica gel was loaded onto a silica gel column and eluted with a solvent system of CH2Cl2/MeOH: 30/1. The fractions containing the product were collected and evaporated to yield 2-amino-7-(2-O-methyl-β-D-ribofuranosyl)-4-methoxy-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (40 mg). This was mixed with 2 N aqueous NaOH (4 mL) and stirred at reflux temperature for 10 h. The mixture was cooled in ice bath, neutralized with 2 N aqueous HCl and evaporated. The solid residue was suspended in MeOH, mixed with silica gel and evaporated. The silica gel was loaded onto a silica gel column and eluted with a solvent system of CH2Cl2/MeOH: 5/1. Appropriate fractions were pooled and evaporated to give the title compound (40 mg) as a white solid.
Workup
- temperatureat reflux temperature for 1.5 h
- temperatureThe mixture was cooled
- additionmixed with silica gel
- customevaporated to dryness
- washeluted with a solvent system of CH2Cl2/MeOH
- additionThe fractions containing the product
- customwere collected
- customevaporated
Sources & evidence
- ORD record
- ord-6ce1f96707d645918d654f18b1af14d8
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481712B2
Reaction notes
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