Potassium Carbonate → HCID 68872956, compound

HRID 2197458Notes

Reaction equation

N[C:2]1([NH2:16])[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]1=[N:4][CH:5]=[N:6]2.C([O-])([O-])=O.[K+].[K+].[O:23]1[CH2:32][CH:24]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[NH2:16][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:32][CH:24]([OH:23])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 6-amino-2-(2-methoxyethoxy)adenine Compound (15) (300 mg, 1.43 mmol) in DMF (3 ml) was added K2CO3. Then (2,3-epoxypropyl)benzene (285 μl, 34 mmol) was added and the reaction mixture was stirred at 70° C. for 5 h. The solvent was removed under vacuum and the residue was washed with brine. The aqueous phase was extracted with DCM and the combined organic layers were dried over Na2SO4, filtered, concentrated, and purified by silica gel chromatography (eluting a linear gradient of 0-10% MeOH in DCM) to give 170 mg of Compound (22). 1H NMR (CDCl3) δ 2.82-2.85 (dd, 2H), δ 3.43 (s, 3H), δ 3.74 (t, 2H), δ 4.00-4.10 (m, 1H), δ 4.25-4.29 (m, 2H), δ 4.42 (t, 2H), δ 5.76 (bs, 2H), δ 7.21-7.34 (m, 5H), δ 7.50 (s, 1H); MS: 494.2 (M+H)+.

Workup

customThe solvent was removed under vacuum
washthe residue was washed with brine
extractionThe aqueous phase was extracted with DCM
dry with materialthe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified by silica gel chromatography (
washeluting a linear gradient of 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-384f38e0edc74624ab8b07d7ea75122e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338593B2

Reaction notes

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