4-Nitrophenol → HCID 58938019, compound

HRID 1011304Notes

Reaction equation

HRID 1011304 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([O-:19])=[O:18].C1N2CCN(CC2)C1.C(N(CC)CC)C>ClCCCl.C(Cl)Cl>[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 9237DabcoHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Product 1

HCID 58938019HCID 58938019, compoundYield 117.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred slurry of 6-chloro-9-(tetrahydro-pyran-2-yl)-9H-purine (2.3 g, 10 mmol, 3 equiv) in anhydrous 1,2-dichloroethane (60 mL) was added a solution of 4-nitrophenol (2.3 g, 10 mmol, 3 equiv), DABCO (1.12 g, 1 mmol, 1 equiv) and triethylamine (3.03 g, 4.18 mL, 3 mmol, 3 equiv) in anhydrous 1,2-dichloroethane (5 mL). The mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with DCM (25 mL), washed with saturated solution of NaHCO3. The aqueous layer was re-extracted with DCM. The combined organic extracts were dried over MgSO4, filtered followed by solvent evaporation, giving 6-(4-nitro-phenoxy)-9-(tetrahydro-pyran-2-yl)-9H-purine (4 g, >99% yield). 1H NMR (400 MHz, CDCl3): δ 8.6 (s, 1H), 8.3 (m, 2H), 8.25 (s, 1H), 7.60 (m, 2H), 5.8 (m, 1H), 4.20 (m, 1H), 3.8 (m, 1H), 2.20 (m, 3H), 1.80 (m, 3H). MS (ESI) for C16H15N5O4: 342 (MH+).

Workup

  1. washwashed with saturated solution of NaHCO3
  2. extractionThe aqueous layer was re-extracted with DCM
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customfollowed by solvent evaporation

Sources & evidence

ORD record
ord-0c024678ce19465e89ac50e20b4b96c1
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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