HCID 178418361, compound → HCID 178521093, compound

HRID 533188Notes

Reaction equation

HRID 533188 reaction equation
C([N:8]([CH2:14][C:15]1[C:19]2[N:20]=[CH:21][N:22]=[C:23]([OH:24])[C:18]=2[NH:17][CH:16]=1)[CH2:9][C@@H:10]([OH:13])[CH2:11][OH:12])C1C=CC=CC=1.[H][H]>O.[Pd]>[OH:24][C:23]1[C:18]2[NH:17][CH:16]=[C:15]([CH2:14][NH:8][CH2:9][C@@H:10]([OH:13])[CH2:11][OH:12])[C:19]=2[N:20]=[CH:21][N:22]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compound2×HCID 178521092HCID 178521092, compound

Product 1

HCID 178521093HCID 178521093, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

(R)-3-(Benzyl((4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)amino)propane-1,2-diol (0.1 g, 0.305 mmol) was dissolved in hot water (20 ml), cooled to rt and 10% Pd—C (50 mg) added. Hydrogen was added from a balloon and the mixture stirred at rt. After 4 h tlc (CH2Cl2-MeOH-cNH3, 5:4.5:0.5) showed reaction over. The hydrogen was replaced with Ar and the mixture heated to 80° C. to ensure product was in solution then the mixture filtered through Celite and the solvent evaporated to give (R)-3-((4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)propane-1,2-diol as a colourless solid (0.072 g, 99%). The product was converted to its hydrochloride salt with 5% HCl. 1H NMR (D2O+DCl, 300 MHz), δ ppm, 9.07 (s, 1H), 7.91 (s, 1H), 4.53 (s, 2H), 4.06 (m, 1H), 3.69-3.57 (m, 2H), 3.33 (dd, 1H, J 12.9, 2.9 Hz), 3.17 (dd, 1H, J 12.9, 9.8 Hz). 13C NMR (D2O+DCl, 75.5 MHz), δ ppm, 153.8 (C), 146.1 (CH), 134.1 (C), 133.1 (CH), 119.6 (C), 104.1 (C), 68.5 (CH), 64.5 (CH2), 50.2 (CH2), 41.8 (CH2). [α]D18 +12.6 (c, 0.565, H2O). +ESMS Found 261.0952 (M+Na)+ C10H14N4O3Na requires 261.0964.

Workup

  1. customreaction over
  2. temperaturethe mixture heated to 80° C.
  3. filtrationthe mixture filtered through Celite
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-1e7269287ffd4a53bac03904d6bf2d56
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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