Thiophenol → HCID 11230343, compound

HRID 497732Notes

Reaction equation

HRID 497732 reaction equation
[F:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.C(N(C(C)C)CC)(C)C.[C:21]1([SH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[F:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([S:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 81531DiisopropylethylamineHCID 52879146-Chloro-2-fluoropurine

Product 1

HCID 11230343HCID 11230343, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-fluoro-6-chloropurine (10.0 g, 57.9 mmol) in methanol (200 mL) is added diisopropylethylamine (25.2 mL, 144.7 mmol). The mixture is cooled to 0° C. and followed by slow addition of thiophenol (11.9 mL, 115.8 mmol) via an addition funnel over one hour. The reaction is stirred at 0° C. for 12 hours. The solvent is then removed under reduced pressure and the solid is collected by filtration and washed twice with hexanes. The collected solid is further purified by re-crystallization from methanol to afford desired product (11.8 g, 83% yield). 1H NMR (400 MHz, (CD3)2SO) δ 7.54 (m, 3H), 7.66(m, 2H), 8.49(s, 1H); MS C11H7FN4S [MH+] 246.04, found: 247.05.

Workup

  1. customThe solvent is then removed under reduced pressure
  2. filtrationthe solid is collected by filtration
  3. washwashed twice with hexanes
  4. customThe collected solid is further purified by re-crystallization from methanol

Sources & evidence

ORD record
ord-cb69779fba3a4be49e56b2e09dfa4b7a
Source dataset
uspto-grants-2005_09
Patent number
US06949644B2

Reaction notes

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