Potassium Carbonate → HCID 86617439, compound

HRID 2197457Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][CH:11]=[N:12]2)=[C:8]([NH2:15])[N:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25][P:26](=[O:33])([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29]>CN(C=O)C>[CH2:31]([O:30][P:26]([CH2:25][CH2:24][CH2:23][N:12]1[CH:11]=[N:10][C:9]2[C:13]1=[N:14][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[N:7][C:8]=2[NH2:15])(=[O:33])[O:27][CH2:28][CH3:29])[CH3:32]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 2-(2-methoxyethoxy)adenine Compound (15) (200 mg, 0.96 mmol) in DMF (5 ml) was added K2CO3 (132 mg 0.96 mmol). Then diethyl (3-bromopropyl)phosphonate (265 μl, 1.44 mmol) was added. The reaction mixture was stirred at 70° C. for 1 h, and the solvent was removed under vacuum. The residue was dissolved in DCM and washed with brine. The aqueous phase was extracted again with DCM. The combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (eluting using a linear gradient of 0-10% MeOH in DCM) to give 293 mg of Compound (19). 1H NMR (CDCl3) δ 1.10-1.16 (m, 6H), δ 1.52-1.59 (m, 2H), δ 1.90-2.09 (m, 2H), δ 3.25 (s, 3H), δ 3.51-3.57 (m, 2H), δ 3.89-3.92 (m, 4H), δ 4.04 (t, 2H), δ 4.28 (t, 2H), δ 6.60 (M, 2H), δ 7.53 (s, 1H); MS: 388.1 (M+H)+, 386.0 (M−1).

Workup

customthe solvent was removed under vacuum
dissolutionThe residue was dissolved in DCM
washwashed with brine
extractionThe aqueous phase was extracted again with DCM
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was purified by silica gel chromatography (
washeluting

Sources & evidence

ORD record: ord-3f7c415e07fa4017a2ad9b2cf3d529a6
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338593B2

Reaction notes

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