CID 6432229 → 7-(((2,2-dimethyl-1,3-dioxan-5-yl)methylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

HRID 533198Notes

Reaction equation

HRID 533198 reaction equation
[CH]Cl.C([N:10]([CH2:20][C:21]1[C:25]2[N:26]=[CH:27][NH:28][C:29](=[O:30])[C:24]=2[NH:23][CH:22]=1)[CH2:11][CH:12]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)C1C=CC=CC=1>CO>[CH3:18][C:15]1([CH3:19])[O:16][CH2:17][CH:12]([CH2:11][NH:10][CH2:20][C:21]2[C:25]3[N:26]=[CH:27][NH:28][C:29](=[O:30])[C:24]=3[NH:23][CH:22]=2)[CH2:13][O:14]1

Participants

4

Reactant 2

HCID 6432229CID 6432229HCID 1358587927-((benzyl((2,2-dimethyl-1,3-dioxan-5-yl)methyl)amino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

Product 1

HCID 1363377787-(((2,2-dimethyl-1,3-dioxan-5-yl)methylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-oneYield 49.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

cHCl was added to a stirred solution of 7-((benzyl((2,2-dimethyl-1,3-dioxan-5-yl)methyl)amino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (50 mg, 131 μmol) in methanol (2 mL). After 0.5 h the reaction was concentrated in vacuo and co-distilled with methanol. The crude reaction was absorbed as a methanol solution onto silica gel and purified by chromatography on silica eluting with 20% 7N NH3/MeOH to afford, presumably, 7-(((2,2-dimethyl-1,3-dioxan-5-yl)methylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (19 mg, 42.4% yield) as a white solid, which was committed to the next step without characterisation. A solution of 7-(((2,2-dimethyl-1,3-dioxan-5-yl)methylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (19 mg, 55.5 μmol) and 10% palladium on carbon (56 mg, 526 μmol) in water (2 mL, 1.11E+05 μmol) was stirred under an atmosphere of hydrogen (0.101 mg, 50.2 μmol) for 72 h. The reaction was filtered through Celite® and the filtrate concentrated in vacuo to yield a crude residue which was purified by chromatography on silica gel, eluting with 5:4.5:0.5 DCM:MeOH:NH4OH to afford 7-((3-hydroxy-2-(hydroxymethyl)propylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one hydrochloride (4 mg, 27.6% yield) as a white solid. 13C NMR (D2O) δ 152.6, 145.0, 133.2, 131.7, 118.4, 102.8, 60.8 (2×CH2), 47.6, 41.1, 39.8.

Workup

  1. concentrationAfter 0.5 h the reaction was concentrated in vacuo and co-distilled with methanol
  2. customThe crude reaction
  3. customwas absorbed as a methanol solution onto silica gel
  4. custompurified by chromatography on silica eluting with 20% 7N NH3/MeOH
  5. customto afford

Sources & evidence

ORD record
ord-bf04c1f56858491c9e52ee1a7df0f69c
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

Loading…