Glycolaldehyde dimer → HCID 178479700, compound

HRID 533202Notes

Reaction equation

HRID 533202 reaction equation
C([BH3-])#N.[Na+].[ClH:5].[OH:6][CH2:7][CH:8]([NH:11][CH2:12][C:13]1[C:17]2[N:18]=[CH:19][NH:20][C:21](=[O:22])[C:16]=2[NH:15][CH:14]=1)[CH2:9][OH:10].[O:23]1CC(O)O[CH2:25][CH:24]1O>CO>[ClH:5].[OH:22][C:21]1[C:16]2[NH:15][CH:14]=[C:13]([CH2:12][N:11]([CH2:25][CH2:24][OH:23])[CH:8]([CH2:7][OH:6])[CH2:9][OH:10])[C:17]=2[N:18]=[CH:19][N:20]=1

Participants

5

Reactant 3

HCID 186078Glycolaldehyde dimerHCID 5003444Sodium cyanoborohydrideHCID 1363377797-((1,3-dihydroxypropan-2-ylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one hydrochloride

Product 1

HCID 178479700HCID 178479700, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (0.011 g, 0.18 mmol) was added to a solution of the product from Example 10.2 (0.041 g, 0.15 mmol) and 1,4-dioxane-2,5-diol (0.027 g, 0.22 mmol, Sigma-Aldrich) in MeOH (3 ml) and stirred at it for 16 h. The solvent was evaporated and the residue chromatographed on silica gel (iPrOH-28% aq. NH4OH-water, 98:1:1) to give the crude product as a yellow solid (˜21 mg). The solid was triturated with a little 7M NH3-EtOH solution to leave the free base form of the title compound as a colourless solid (˜12 mg). This solid was dissolved in excess 5% aq. HCl then the solvent evaporated to give 7-(((1,3-dihydroxypropan-2-yl)(2-hydroxyethyl)amino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one hydrochloride as a solid (15 mg, 32%). 1H NMR (D2O, referenced to HOD at 4.72 ppm) δ 8.49 (s, 1H), 7.82 (s, 1H), 4.77 (s, 2H), 3.98-3.88 (m, 6H), 3.77 (sextet, J=6.1 Hz, 1H), 3.56 (br. s, 2H). 13C NMR (D2O), δ 154.4, 144.4, 139.5, 132.8, 118.6, 104.1, 64.3, 56.7, 55.7, 52.6, 47.1. +ESMS Found 283.1407 (M+H)+ C12H19N4O4 requires 283.1406.

Workup

  1. customThe solvent was evaporated
  2. customthe residue chromatographed on silica gel (iPrOH-28% aq. NH4OH-water, 98:1:1)
  3. customto give the crude product as a yellow solid (˜21 mg)
  4. customThe solid was triturated with a little 7M NH3-EtOH solution

Sources & evidence

ORD record
ord-2e4cf9b1e4f7497e9e9a4e0dbf9f37a6
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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