Sodium hydride → HCID 22851232, compound

HRID 1463785Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[H-].[Na+].[CH:14]([O:17][P:18]([CH2:24][O:25][C@@H:26]([CH3:33])[CH2:27]OS(C)(=O)=O)([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])([CH3:16])[CH3:15]>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:33][C@@H:26]([O:25][CH2:24][P:18]([O:20][CH:21]([CH3:23])[CH3:22])([O:17][CH:14]([CH3:16])[CH3:15])=[O:19])[CH3:27])=[C:4]([Cl:11])[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Amino-6-chloropurine (1.40 g, 8.3 mmol) was added portionwise to a slurry of sodium hydride (0.25 g, 80% dispersion in oil, 8.3 mmol) in dimethylformamide (50 mL) at room temperature. Vigorous bubbling was noted during the addition. After 30 minutes, the clear, yellow solution was treated with a solution of (S)-2-O-[(diisopropylphosphono)methyl]-1-O-methanesulfonyl-1,2-propanediol (2.50 g, 7.5 mmol) in dimethylformamide (5 mL), and the reaction mixture was heated to 100° C. After 5 hours, the mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was purified by column chromatography on silica gel (20:1, 2% to 4% to 8% methanol/methylene chloride) to provide 1.89 g (62%) of the title compound as a viscous pale yellow oil.

Workup

customVigorous bubbling
additionwas noted during the addition
waitAfter 5 hours
temperatureto cool to room temperature
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel (20:1, 2% to 4% to 8% methanol/methylene chloride)

Sources & evidence

ORD record: ord-fc53935fb9eb4a5ba5063c8245c41d28
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05302585

Reaction notes

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