N-bromobutanimide → HCID 11508877, compound

HRID 1173530Notes

Reaction equation

HRID 1173530 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]3[NH:19][C:18]4[C:13](=[N:14][C:15]([F:21])=[N:16][C:17]=4[NH2:20])[N:12]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C1C(=O)N([Br:29])C(=O)C1>CN(C=O)C>[F:21][C:15]1[N:14]=[C:13]2[C:18]([NH:19][C:11]([CH2:10][C:8]3[C:7]([Br:29])=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)=[N:12]2)=[C:17]([NH2:20])[N:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11601676HCID 11601676, compound

Product 1

HCID 11508877HCID 11508877, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-Benzo[1,3]dioxol-5-ylmethyl-2-fluoroadenine (45 mg, 0.157 mmol), NBS (56 mg, 0.314 mmol) in DMF (0.5 mL) was stirred at room temperature for 1.5 h. Following solvent removal, product (20 mg, 34.8%) was collected through silica gel column purification (CHCl3:EtOAc at 9:1 to 4:6). 1H NMR (400 MHz, acetone-d6) 7.51 (bs, 2H), 7.21 (s, 1H), 6.98 (s, 1H), 6.06 (s, 2H), 4.13 (s, 2H); MS m/z 366.0 (M+H)+.

Workup

  1. customFollowing solvent removal, product (20 mg, 34.8%)
  2. customwas collected through silica gel column purification (CHCl3:EtOAc at 9:1 to 4:6)

Sources & evidence

ORD record
ord-8bf29ba855894ee4b48276368c520781
Source dataset
uspto-grants-2010_11
Patent number
US07834181B2

Reaction notes

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