Hydrochloric Acid → HCID 50996967, compound

HRID 1399594Notes

Reaction equation

HRID 1399594 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([C:11]2[C:16]([CH:17]([CH2:22][CH2:23][CH3:24])[C:18]([O:20]C)=[O:19])=[C:15]([CH3:25])[N:14]=[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:12]=2)[CH:8]=[CH:9][CH:10]=1.Cl.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:6]=[C:7]([C:11]2[C:16]([CH:17]([CH2:22][CH2:23][CH3:24])[C:18]([OH:20])=[O:19])=[C:15]([CH3:25])[N:14]=[C:13]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:12]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66955906HCID 66955906, compound

Product 1

HCID 50996967HCID 50996967, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2-(4-(3-(methoxymethoxy)phenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (60 mg; 0.143 mmol) was dissolved in methanol (1.5 mL) and 12N hydrochloric acid (10 μL; 0.120 mmol) was added. The mixture was heated at 60° C. for 3 h until the deprotection was finished (monitored by TLC). The mixture was basified with an excess 10N sodium hydroxide solution and stirred in a sealed tube at 80° C. for 18 h. The volatiles were removed under reduced pressure, the residue was dissolved in water and acidified with a 6N hydrochloric acid solution. The precipitate was filtered, washed with water and dried under reduced pressure over phosphorus pentoxide to give 37 mg (71%) of the title compound as a yellowish solid. ESI/APCI(+): 363 (M+H). ESI/APCI(−): 723 (2M−H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-fc143a0062df4f64bf1595e456485989
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

Loading…