Ammonium formate → HCID 58938018, compound

HRID 1011305Notes

Reaction equation

HRID 1011305 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[N:17]=[CH:16][N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>C(O)C>[O:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH:18]1[N:13]1[CH:12]=[N:11][C:10]2[C:14]1=[N:15][CH:16]=[N:17][C:9]=2[O:8][C:7]1[CH:24]=[CH:25][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 58938019HCID 58938019, compound

Product 1

HCID 58938018HCID 58938018, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 6-(4-nitro-phenoxy)-9-(tetrahydro-pyran-2-yl)-9H-purine (4 g, 12.86 mmol, 1.0 eq.), 5% PtS (20% by weight, 800 mg), ammonium formate (3.2 g, 51.44 eq), and ethanol (100 ml). The reaction was stirred at reflux for 30 min upon which the reaction was filtered hot through celite. Removal of the ethanol was followed by the addition of 1N HCl, which was further washed twice with DCM (50 ml). The aqueous layer was basified and extracted with DCM. The organic layer was then washed twice with brine (50 ml) and dried over sodium sulfate. After removal of the DCM in vacuo, 4-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yloxy]-phenylamine was obtained (3 g, 83%) as a solid. 1H NMR (400 MHz, CDCl3): δ 8.4 (s, 1H), 8.2 (s, 1H), 7.0 (m, 2H), 6.75 (m, 2H), 5.8 (m, 1H), 4.20 (m, 1H), 4.0 (m, 2H), 3.8 (m, 1H), 2.20 (m, 3H), 1.80 (m, 3H). MS (ESI) for C16H17N5O2: 312 (MH+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. temperatureat reflux for 30 min upon which the reaction
  3. filtrationwas filtered hot through celite
  4. customRemoval of the ethanol
  5. additionwas followed by the addition of 1N HCl, which
  6. washwas further washed twice with DCM (50 ml)
  7. extractionextracted with DCM
  8. washThe organic layer was then washed twice with brine (50 ml)
  9. dry with materialdried over sodium sulfate
  10. customAfter removal of the DCM in vacuo

Sources & evidence

ORD record
ord-2f35b9180e6d4406a23bc04b5af42c74
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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