1,3-Dibromopropane → HCID 67115624, compound

HRID 521593Notes

Reaction equation

HRID 521593 reaction equation
BrC[CH2:3][CH2:4][N:5]1[C:13]([S:14][C:15]2[C:24]([I:25])=[CH:23][C:18]3[O:19][CH2:20][CH2:21][O:22][C:17]=3[CH:16]=2)=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:26].[Br:27]CCCBr.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:27][CH2:3][CH2:4][N:5]1[C:13]([S:14][C:15]2[C:24]([I:25])=[CH:23][C:18]3[O:19][CH2:20][CH2:21][O:22][C:17]=3[CH:16]=2)=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:26]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 67115575HCID 67115575, compound

Product 1

HCID 67115624HCID 67115624, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-(3-Bromopropyl)-8-(7-iodo-2,3-dihydrobenzo[b][1,4]dioxin-6-ylthio)-9H-purin-6-amine (S9-5). A mixture of S9-3 (0.213 g, 0.5 mmol), 1,3-dibromopropane (0.512 g, 2.5 mmol) and Cs2CO3 (0.184 g, 0.75 mmol) in anhydrous DMF (6 mL) was stirred at room temperature for 3 h. Solids were filtered and the filtrate was condensed under reduced pressure to give a residue that was purified by preparative thin layer chromatography (CHCl3:MeOH—NH3 (7N), 20:1) to give S9-5 (0.104 g, 38%). 1H NMR (CDCl3, 500 MHz) δ 8.26 (s, 1H), 7.32 (s, 1H), 6.94 (s, 1H), 5.6 (br s, 2H), 4.27 (t, J=7.0 Hz, 2H), 4.10-4.17 (m, 4H), 3.32 (t, J=7.0 Hz, 2H), 2.26 (m, 2H); MS (ESI) m/z 547.9/549.8 [M+H]+.

Workup

  1. filtrationSolids were filtered
  2. customcondensed under reduced pressure
  3. customto give a residue that
  4. customwas purified by preparative thin layer chromatography (CHCl3:MeOH—NH3 (7N), 20:1)
  5. customto give S9-5 (0.104 g, 38%)

Sources & evidence

ORD record
ord-46cd974e4d93470aa9db671efb88af78
Source dataset
uspto-grants-2016_05
Patent number
US09328114B2

Reaction notes

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