8-Bromoadenine → HCID 57850140, compound

HRID 736665Notes

Reaction equation

HRID 736665 reaction equation
[Br:1][C:2]1[NH:10][C:9]2[C:4](=[N:5][CH:6]=[N:7][C:8]=2[NH2:11])[N:3]=1.[C:12]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:17][CH2:16]1)(=[O:14])[CH3:13]>C1COCC1>[C:12]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][N:3]2[C:2]([Br:1])=[N:10][C:9]3[C:4]2=[N:5][CH:6]=[N:7][C:8]=3[NH2:11])[CH2:17][CH2:16]1)(=[O:14])[CH3:13].[C:12]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][N:5]2[C:4]3[C:9]([N:10]=[C:2]([Br:1])[N:3]=3)=[C:8]([NH2:11])[N:7]=[CH:6]2)[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 814578-BromoadenineHCID 57850813HCID 57850813, compound

Product 2

HCID 57850140HCID 57850140, compoundYield 42%HCID 178473805HCID 178473805, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 8-bromoadenine (0.042 g, 0.197 mmol) and toluene-4-sulfonic 2-(1-acetyl-piperidin-4-yl)-ethyl ester (0.077 g, 0.237 mmol) in THF was added Barton's base (50 μl, 0.237 mmol) at room temperature. The reaction mixture was heated at 100° C. for 15 min in microwave reactor, at the end of this period reaction was cooled to room temperature and the crude was purified by Isco silica gel flash column using 0-5% gradient of methanol in dichloromethane to give 0.030 g (42%) of 9-[2-(1-acetylpiperidin-4-yl)-ethyl]-8-bromo-9H-purin-6-amine, LC-MS [M+H]+ 366.2 and 0.015 g (21%) of 3-[2-(1-acetylpiperidin-4-yl)-ethyl]-8-bromo-3H-purin-6-amine, LC-MS [M+H]+ 366.2

Workup

  1. temperaturewas cooled to room temperature
  2. customthe crude was purified by Isco silica gel flash column

Sources & evidence

ORD record
ord-638c3532342e4d4ca91d685bb770235b
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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