Hydrochloric Acid → 2-Amino-7-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

HRID 448688Notes

Reaction equation

HRID 448688 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:6]=2[N:7]=1.Cl.[OH-:23].[Na+]>>[NH2:1][C:2]1[NH:3][C:4](=[O:23])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11483860(2R,3R,4R,5R)-2-(2-amino-4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol

Product 1

HCID 1354296822-Amino-7-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

Procedure

A mixture of product from Step B (90 mg, 0.3 mmol) in aqueous NaOH (2N, 9 mL) was heated at reflux temperature for 5 h, then neutralized at 0° C. with 2 N aqueous HCl and evaporated to dryness. Purification on a silica gel column with CH2Cl2/MeOH, 5/1 as eluent afforded the title compound as a white solid (70 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 h
  3. customevaporated to dryness
  4. customPurification on a silica gel column with CH2Cl2/MeOH, 5/1 as eluent

Sources & evidence

ORD record
ord-5988d88563884b4891156262da6a2798
Source dataset
uspto-grants-2013_07
Patent number
US08481712B2

Reaction notes

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