Hydrochloric Acid → HCID 59126898, compound

HRID 1969365Notes

Reaction equation

HRID 1969365 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): 1H NMR (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-6182684c5ba849dc9a191cdb546f34e9
Source dataset
uspto-grants-2013_04
Patent number
US08426591B2

Reaction notes

Loading…