HCID 135858790, compound → HCID 135858823, compound

HRID 533195Notes

Reaction equation

HRID 533195 reaction equation
C([N:8]([CH2:14][C:15]1[C:19]2[N:20]=[CH:21][NH:22][C:23](=[O:24])[C:18]=2[NH:17][CH:16]=1)[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])C1C=CC=CC=1>C(O)(C)C.[Pd]>[OH:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][CH2:14][C:15]1[C:19]2[N:20]=[CH:21][NH:22][C:23](=[O:24])[C:18]=2[NH:17][CH:16]=1

Participants

4

Reactant 1

HCID 135858790HCID 135858790, compound

Product 1

HCID 135858823HCID 135858823, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

To 7-((benzyl(4-hydroxybutyl)amino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (230 mg, 0.70 mmol) in iso-propanol (3 ml) was added 10% Pd—C (50 mg). The mixture was stirred at 50° C. under an atmospheric pressure of H2 overnight. Then the solution was filtered on a pad of Celite and the pad washed with MeOH (10 ml). The filtrate was evaporated to dryness and the residue was chromatographed on silica (DCM-MeOH 8:2+1% cNH3) to give 7-(((4-hydroxybutyl)amino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (133 mg, 0.56 mmol, 80% yield) as a white solid. 1H NMR (300 MHz, CD3OD+DCl) 1.64 (2H, m), 1.87 (2H, m), 3.19 (2H, t, J 7.6 Hz), 3.63 (2H, t, J 5.9 Hz), 4.48 (2H, s), 7.87 (1H, s), 9.05 (1H, s); 13C NMR (75 MHz, CD3OD+DCl) 24.7, 30.7, 30.9, 42.1, 62.5, 105.6, 120.2, 133.4, 133.8, 146.8, 153.3.

Workup

  1. filtrationThen the solution was filtered on a pad of Celite
  2. washthe pad washed with MeOH (10 ml)
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was chromatographed on silica (DCM-MeOH 8:2+1% cNH3)

Sources & evidence

ORD record
ord-76d6d2daddef43409c1899438edf8eb1
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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