Potassium Carbonate → HCID 66798808, compound

HRID 1193396Notes

Reaction equation

HRID 1193396 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[CH3:11][N:12]([CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:10][O:9][C:4]1[N:3]=[C:2]([N:26]2[CH2:25][CH2:24][CH:23]([N:12]([CH3:11])[C:13](=[O:22])[O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:28][CH2:27]2)[CH:7]=[C:6]([CH3:8])[N:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 134258364-Chloro-2-methoxy-6-methylpyrimidineHCID 18677746Benzyl methyl(piperidin-4-yl)carbamate

Product 1

HCID 66798808HCID 66798808, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-chloro-2-methoxy-6-methylpyrimidine (300 mg, 1.8987 mmol, 1 eq), benzyl methyl(piperidin-4-yl)carbamate (stage 3 AMN-52) (470 mg, 1.8987 mmol, 1 eq) and K2CO3 (523 mg, 3.796 mmol, 2 eq) in acetone (10 ml) was refluxed for 16 h. When the reaction was complete according to TLC monitoring, filtration over Celite was carried out and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 2% methanol/dichloromethane). The desired product was in the form of a light-yellow solid. Yield: 71% (500 mg, 1.3513 mmol)

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationWhen the reaction was complete according to TLC monitoring, filtration over Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by column chromatography (silica gel, 2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-c650793b5ff1464aa194293de14e18b8
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…