HCID 178432480, compound → HCID 178432481, compound

HRID 1371137Notes

Reaction equation

HRID 1371137 reaction equation
[CH3:1][C:2]1[NH:7][C:6]2=[CH:8][C:9]([C:11]3[CH:12]=[CH:13][CH2:14][CH2:15][CH:16]=3)=[N:10][C:5]2=[C:4]([C:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=2)[N:3]=1>C(O)C.O=[Pt]=O>[CH:17]1([C:4]2[N:3]=[C:2]([CH3:1])[NH:7][C:6]3=[CH:8][C:9]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[N:10][C:5]=23)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

4

Reactant 1

HCID 178432480HCID 178432480, compound

Product 1

HCID 178432481HCID 178432481, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-methyl-4-(1-cyclohexenyl)-5H-6-phenylpyrrolo[3,2-d]pyrimidine (Example 59) (96 mg, 0.33 mmol) in ethanol (5 mL) was agitated on a Parr Apparatus at room temperature in the presence of PtO2 (Aldrich Chemical Company) (20 mg, 0.088 mmol) under H2 (70 psi) for 30 h. The reaction mixture was filtered through a pad of Celite and concentrated on a rotary evaporator. Chromatography on silica gel with a gradient eluant of EtOAc (0-20%):hexanes (100-80%) afforded 55 mg (57%) of the title compoud as an off-white solid. Mp: >280° C. 1H NMR (CDCl3; 400 MHz): δ 1.44-1.49 (m, 2), 1.81-1.88 (m, 4), 1.93-2.01 (m, 4), 2.99 (m, 1), 6.86 (d, 1, J=1.4), 7.44 (t, 1, J=6.1), 7.51 (t, 2, J=6.1), 7.74 (d, 2, J=6.1), 8.40 (s, 1). MS m/z: 292 (M+1), 290 (M−1). HRMS: Calcd for M+H: 292.1814. Found: 292.1806.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated on a rotary evaporator
  3. customChromatography on silica gel with a gradient eluant of EtOAc (0-20%):hexanes (100-80%) afforded 55 mg (57%) of the title compoud as an off-white solid

Sources & evidence

ORD record
ord-b21e81b9914f4223b1ee41973963bb93
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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