Adenine → HCID 178508641, compound

HRID 1727325Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]1[CH2:14][C@H:13](CS([O-])(=O)=O)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:20]1[C:28]([NH2:29])=[C:27]2[C:23]([N:24]=[CH:25][NH:26]2)=[N:22][CH:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:8][CH2:9][CH2:10][C@@H:11]1[CH2:12][C@H:13]([N:24]2[CH:25]=[N:26][C:27]3[C:23]2=[N:22][CH:21]=[N:20][C:28]=3[NH2:29])[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In a 25 mL three-neck flask with trans-3-(benzyloxyethyl)cyclobutyl-mesylate (0.50 g, 1.76 mmol), adenine (0.35 g, 2.59 mmol) and Cs2CO3 (0.86 g, 2.64 mmol) inside, dry DMF 8 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 0.24 g (43%) the desired product. 1H NMR (CDCl3, 300 MHz): δ 1.84-1.92 (m, 2H), 2.16-2.46 (m, 3H), 2.68-2.80 (m, 2H), 3.48-3.52 (t, J=6.3, 2H), 4.51 (s, 2H), 4.80-4.92 (m, 1H), 7.88 (s, 1H), 8.35 (s, 1H). MS (FAB): expected for C18H21N5O (M+H)+ 324.39. Found 324.18195. IR (neat) νmax 3398, 2927, 2862, 1718, 1453, 1315, 1276, 1113, 1071, 1027, 738, 714, 698.

Workup

customthe solvent was removed

Sources & evidence

ORD record: ord-35313f6e8253401295347491ddd7667d
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495006B2

Reaction notes

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