Trifluoroacetic acid → HCID 178508685, compound

HRID 521599Notes

Reaction equation

HRID 521599 reaction equation
F[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:11][C:12]3[C:20](I)=[CH:19][C:15]4[CH2:16][CH2:17][O:18][C:14]=4[CH:13]=3)[NH:8]2)=[C:4]([NH2:22])[N:3]=1.C(O)(C(F)(F)F)=O.C1C(=O)[N:34](I)C(=O)C1>C(#N)C>[O:18]1[C:14]2[CH:13]=[C:12]([CH2:11][C:7]3[NH:8][C:9]4[C:5]([N:6]=3)=[C:4]([NH2:22])[N:3]=[C:2]([NH2:34])[N:10]=4)[CH:20]=[CH:19][C:15]=2[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 178508566HCID 178508566, compound

Product 1

HCID 178508685HCID 178508685, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-fluoro-8-((5-iodo-2,3-dihydrobenzofuran-6-yl)methyl)-9H-purin-6-amine (S16-9). To a suspension of S16-8 (0.45 g, 1.6 mmol) in 50 mL acetonitrile was added 1 mL of TFA. To the resulting solution was added NIS (1.06 g, 4.7 mmol) and the reaction mixture was stirred at rt for 3 h. It was then evaporated to dryness and purified by flash chromatography to give S16-9 (0.408 g, 63%) as a yellow solid. 1H NMR (500 MHz, MeOH-d4) δ 7.67 (s, 1H), 6.76 (s, 1H), 4.59 (m, 2H), 4.28 (s, 2H), 3.21 (m, 2H); MS: m/z 412 (M+H)+.

Workup

  1. customIt was then evaporated to dryness
  2. custompurified by flash chromatography
  3. customto give S16-9 (0.408 g, 63%) as a yellow solid

Sources & evidence

ORD record
ord-521f372b47b64636b9fcd5043b3c3303
Source dataset
uspto-grants-2016_05
Patent number
US09328114B2

Reaction notes

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