Hydrochloric Acid → HCID 59126898, compound

HRID 1988554Notes

Reaction equation

HRID 1988554 reaction equation
C[O:2][C:3]([C:5]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:11]=[C:10]2[C:6]=1[N:7](C)[CH:8]=[N:9]2)=[O:4].Cl.C(OCC)(=O)C>[OH-].[Na+]>[NH2:9][C:10]1[N:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]=1[NH:7][CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 59126926HCID 59126926, compound

Product 1

HCID 59126898HCID 59126898, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-(4-Chloro-2-fluoro-3-methoxyphenyl)-7-methyl-7H-purine-6-carboxylic acid methyl ester (200 mg, 0.57 mmol) was slurried in 2M sodium hydroxide (10 mL) and heated at reflux for 2 h. After cooling, the pH was adjusted to 4 with 1M HCl. The precipitated solid was dissolved by shaking the mixture with two portions of ethyl acetate (45 mL each). The combined organic phases were washed with brine, dried and evaporated to give the title compound (100 mg, 53% yield): 1HNMR (DMSO-d6) δ 7.62 (dd, 1H), 7.36 (dd, 1H), 7.05 (br s, 2H), 3.97 (m, 1H), 3.91 (s, 3H), 2.17 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. dissolutionThe precipitated solid was dissolved
  5. washThe combined organic phases were washed with brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-8273f7f9c799421a87a69488eefd2041
Source dataset
uspto-grants-2010_01
Patent number
US07642220B2

Reaction notes

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