Thiophenol → HCID 135848039, compound

HRID 497733Notes

Reaction equation

HRID 497733 reaction equation
Br[C:2]1[NH:3][C:4](=[O:11])[C:5]2[NH:6][CH:7]=[N:8][C:9]=2[N:10]=1.[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C>CO>[C:12]1([S:18][C:2]2[NH:3][C:4](=[O:11])[C:5]3[NH:6][CH:7]=[N:8][C:9]=3[N:10]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 81531DiisopropylethylamineHCID 1354139912-Bromohypoxanthine

Product 1

HCID 135848039HCID 135848039, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-bromohypoxanthine (10.0 g, 46.5 mmol) in methanol (200 mL) was added thiophenol (9.55 mL, 93.0 mmol) and diisopropylethylamine (20.2 mL, 116.3 mmol). The reaction was stirred at 90° C. for overnight. The solvent was removed under reduced pressure and the solid was collected by filtration and washed with hexanes (100 mL×2). The collected solid was further purified by re-crystallization from methanol to afford desired product (10.1 g, 89% yield). 1H NMR (400 MHz, (CD3)2SO) δ 7.50(m, 3H), 7.62 (m, 2H), 7.97 (s, 1H); MS (ES) calc'd for C11H8N4OS [MH+] 245.05, found: 245.05.

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationthe solid was collected by filtration
  3. washwashed with hexanes (100 mL×2)
  4. customThe collected solid was further purified by re-crystallization from methanol

Sources & evidence

ORD record
ord-3cd206fad53947e287acbe04867c2495
Source dataset
uspto-grants-2005_09
Patent number
US06949644B2

Reaction notes

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