Hydrochloric Acid → HCID 178508437, compound

HRID 2074202Notes

Reaction equation

HRID 2074202 reaction equation
C(=O)(OC)[O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[C:17](=[O:18])[NH:16][C:15]3[C:10]2=[N:11][C:12]([NH2:20])=[N:13][C:14]=3[Cl:19])[CH2:5][CH2:4]1.Cl>[OH-].[K+]>[NH2:20][C:12]1[N:11]=[C:10]2[C:15]([NH:16][C:17](=[O:18])[N:9]2[C@H:6]2[CH2:5][CH2:4][C@H:3]([OH:2])[CH2:8][CH2:7]2)=[C:14]([Cl:19])[N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178502570HCID 178502570, compound

Product 1

HCID 178508437HCID 178508437, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Trans-4-(2-Amino-6-chloro-8-oxo-7,8-dihydropurin-9-yl)cyclohexyl methyl carbonate (1.43 g) was dissolved in 80 mL of an aqueous solution 0.5 N KOH and the reaction mixture heated at reflux for 30 min (LC-MS analysis indicated reaction to be complete). The reaction mixture was then cooled in an ice bath, and its pH was brought to 7 by drop wise addition of a concentrated aqueous solution of HCl. A light pink solid precipitated. It was filtered under vacuum, thoroughly dried in vacuum oven at 60° C., to give the desired product in 86% yield. 1H NMR (300 MHz, CDCl3+CD3OD) δ, ppm: 8.48 (br s, 1H), 7.73 (s, 2H), 4.26-4.18 (m, 1H), 3.70-3.61 (m, 1H), 2.53-2.40 (m, 2H), 2.10-2.06 (m, 2H), 1.81-1.76 (m, 2H), 1.48-1.37 (m, 2H); MS (EI) m/z 284.1 (MH)+.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 30 min
  3. custom(LC-MS analysis indicated reaction to be complete)
  4. temperatureThe reaction mixture was then cooled in an ice bath
  5. customA light pink solid precipitated
  6. filtrationIt was filtered under vacuum
  7. customthoroughly dried in vacuum oven at 60° C.

Sources & evidence

ORD record
ord-64fc721a4d5d4f5baa2ddfcdcf55d803
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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