Boron tribromide → HCID 178520893, compound

HRID 533194Notes

Reaction equation

HRID 533194 reaction equation
B(Br)(Br)Br.C([O:12]C[N:14]1[C:22]2[C:21]([O:23]C)=[N:20][CH:19]=[N:18][C:17]=2[C:16]([CH2:25][NH:26][C:27]([CH2:32][OH:33])([CH2:30][OH:31])[CH2:28][OH:29])=[CH:15]1)C1C=CC=CC=1>ClCCl.CO>[NH4+:14].[OH-:12].[OH:23][C:21]1[C:22]2[NH:14][CH:15]=[C:16]([CH2:25][NH:26][C:27]([CH2:30][OH:31])([CH2:32][OH:33])[CH2:28][OH:29])[C:17]=2[N:18]=[CH:19][N:20]=1

Participants

6

Reactant 2

HCID 25134Boron tribromideHCID 252232862-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(hydroxymethyl)propane-1,3-diol

Product 2

HCID 14923Ammonium HydroxideHCID 178520893HCID 178520893, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1 mL, 1.0 mmol) was added dropwise to a solution of 2-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(hydroxymethyl)propane-1,3-diol (30 mg, 74.5 μmol) in dichloromethane (5 mL) and stirred at r.t. A white solid precipitated from the reaction after 1 h and the reaction was then quenched with methanol, concentrated in vacuo and co-distilled with methanol (3×25 mL) to afford a crude residue. The residue was dissolved in methanol absorbed onto silica and chromatographed eluting with 5:4.5:0.5 DCM:MeOH:NH4OH to afford 2-((4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(hydroxymethyl)propane-1,3-diol (7 mg, 26.1 μmol, 35.0% yield) as a white solid which was converted to the HCl salt for NMR analysis. Mpt 223-224° C. (plates from EtOH). 1H NMR (D2O, referenced to internal acetone at 2.225 ppm) δ 9.06, (s, 1H), 7.92 (s, 1H), 4.59 (s, 2H), 3.91 (s, 6H). 13 NMR (D2O, referenced to internal acetone at δ 31.5) δ 153.7, 146.0, 134.2, 133.0, 119.4, 104.7, 67.6, 59.3, 36.4. +ESMS Found 269.1263 (M+H)+ C11H17N4O4 requires 269.1250.

Workup

  1. customA white solid precipitated from the reaction after 1 h
  2. customthe reaction was then quenched with methanol
  3. concentrationconcentrated in vacuo and co-distilled with methanol (3×25 mL)
  4. customto afford a crude residue
  5. customabsorbed onto silica
  6. customchromatographed
  7. washeluting with 5:4.5:0.5 DCM

Sources & evidence

ORD record
ord-5a5b09708f964867aed88bd68a963f7e
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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