Hydrochloric Acid → HCID 178499413, compound

HRID 1684985Notes

Reaction equation

[Na].Cl[C:3]1[N:11]=[C:10]2[C:6]([N:7]=[C:8]([OH:24])[N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:14]=2)=[C:5]([NH2:25])[N:4]=1.Cl.[S:27](=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH2:37]([OH:39])[CH3:38]>CO>[OH:24][C:8]1[N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:14]=2)[C:10]2[C:6]([N:7]=1)=[C:5]([NH2:25])[N:4]=[C:3]([S:27][CH2:38][CH2:37][OH:39])[N:11]=2

Participants

Conditions

Temperature: 120 °C

Procedure

Sodium (67 mg, 2.90 mmol) was dissolved in 2-mercapt ethanol (2.5 ml) and thereto was added 2-chloro-8-hydroxy-9-(3-methoxycarbonylmethylbenzyl)adenine (100 mg, 0.29 mmol) obtained by Example 98. The mixture was stirred at 120° C. for 4 hours and then neutralized with 12N hydrochloric acid. After removing the solvent, to the residue were added methanol (3.0 ml) and concentrated sulfuric acid (0.14 g, 1.43 mmol), and the mixture was refluxed for 30 minutes. The solution was neutralized with saturated sodium hydrogencarbonate solution and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated. To the residue was added water, the mixture was filtered and washed with water to give the captioned compound (55 mg, 0.14 mmol, yield: 49%) as a white solid.

Workup

customAfter removing the solvent
temperaturethe mixture was refluxed for 30 minutes
extractionextracted with chloroform
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated
additionTo the residue was added water
filtrationthe mixture was filtered
washwashed with water

Sources & evidence

ORD record: ord-decf8aec263f4697b2c3936cc897d99f
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148371B2

Reaction notes

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