Water → 9-((3aR,4R,6R,6aR)-6-(((3-(azidomethyl)cyclobutyl)(methyl)amino)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine

HRID 511584Notes

Reaction equation

CS(O[CH2:6][CH:7]1[CH2:10][CH:9]([N:11]([CH2:13][C@@H:14]2[C@@H:21]3[C@@H:17]([O:18][C:19]([CH3:23])([CH3:22])[O:20]3)[C@H:16]([N:24]3[CH:32]=[N:31][C:30]4[C:25]3=[N:26][CH:27]=[N:28][C:29]=4[NH2:33])[O:15]2)[CH3:12])[CH2:8]1)(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+].O>CN(C=O)C>[N:34]([CH2:6][CH:7]1[CH2:8][CH:9]([N:11]([CH2:13][C@@H:14]2[C@H:21]3[O:20][C:19]([CH3:22])([CH3:23])[O:18][C@H:17]3[C@H:16]([N:24]3[CH:32]=[N:31][C:30]4[C:25]3=[N:26][CH:27]=[N:28][C:29]=4[NH2:33])[O:15]2)[CH3:12])[CH2:10]1)=[N+:35]=[N-:36]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)methyl methane sulfonate (150 mg, 0.31 mmol) in DMF (3 ml) was added NaN3 (81 mg, 1.24 mmol). The mixture was heated at 70° C. for 3 h. Water (30 ml) was added and the mixture was extracted with ethyl acetate (20 ml×3). The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by Prep-TLC (DCM:MeOH=30:1) to obtain the title compound (90 mg, Yield 67%). ESI-MS (m/z): 430.2[M+1]+.

Workup

extractionthe mixture was extracted with ethyl acetate (20 ml×3)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated
customThe residue was purified by Prep-TLC (DCM:MeOH=30:1)

Sources & evidence

ORD record: ord-2ab31895d8724df28236bc5bc472720b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096634B2

Reaction notes

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