Adenine → HCID 178445819, compound

HRID 1641518Notes

Reaction equation

[CH:1]([CH:4]([C@H:14]1[CH2:17][C@H:16](CS([O-])(=O)=O)[CH2:15]1)[C:5]([CH:11]([CH3:13])[CH3:12])([CH:8]([CH3:10])[CH3:9])[O:6][SiH3:7])([CH3:3])[CH3:2].[N:23]1[C:31]([NH2:32])=[C:30]2[C:26]([N:27]=[CH:28][NH:29]2)=[N:25][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:1]([CH:4]([C@@H:14]1[CH2:15][C@H:16]([N:27]2[CH:28]=[N:29][C:30]3[C:26]2=[N:25][CH:24]=[N:23][C:31]=3[NH2:32])[CH2:17]1)[C:5]([CH:8]([CH3:9])[CH3:10])([CH:11]([CH3:12])[CH3:13])[O:6][SiH3:7])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

In a 25 mL three-neck flask with trans-3-(triisopropyl-siloxyethyl)cyclobutyl-mesylate (0.27 g, 7.7 mmol), adenine (0.16 g, 1.18 mmol) and Cs2CO3 (0.38 g, 1.17 mmol) inside, dry DMF 5 mL was added under argon. Then began to heat to 120° C. and after 24 hr, the solvent was removed and directly applied to silica gel flash chromatography to give 0.14 g (47%) the desired product. 1H NMR (CDCl3, 400 MHz): δ 0.99-1.05 (m, 21H), 1.72-1.78 (m, 2H), 2.15-2.23 (m, 2H), 2.60-2.79 (m, 3H), 3.67-3.70 (t, J=6.0, 2H), 4.81-4.90 (m, 1H), 6.37-6.39 (bs, 2H), 7.88 (s, 1H), 8.31 (s, 1H). 13C NMR (CDCl3, 100 MHz): δ 12.08, 18.17, 26.60, 37.03, 39.84, 45.86, 61.64, 138.76, 140.09, 150.07, 152.91, 155.93. MS (FAB): expected for C20H35N5OSi (M+H)+ 390.61. Found 390.26828. IR (neat) νmax 2942, 2865, 1670, 1604, 1571, 1463, 1415, 1308, 1246, 1108, 882, 681, 658.

Workup

customthe solvent was removed

Sources & evidence

ORD record: ord-253cb6d67ba0474ca2805980faea6552
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114994B2

Reaction notes

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