Glycine → N-(5-methoxypyrimidin-2-yl)hexanamide

HRID 1442502Notes

Reaction equation

HRID 1442502 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]([NH2:9])=[N:7][CH:8]=1.[C:10](Cl)(=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].NCC(O)=O>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]([NH:9][C:10](=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 750GlycineHCID 67340Hexanoyl chlorideHCID 23052442-Amino-5-methoxypyrimidine

Product 1

HCID 57346488N-(5-methoxypyrimidin-2-yl)hexanamideYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Methoxypyrimidin-2-amine (12.3 g, 98.3 mmol) was dissolved in pyridine (123 mL), the solution was added with hexanoyl chloride (14.5 g, 108 mmol) on an ice bath, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added with 1 M aqueous glycine (98.3 mL) at 0° C., and the mixture was stirred for 1 hour, and then extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, and the resulting residue was azeotroped with toluene. The resulting residue was recrystallized from chloroform-hexane to obtain N-(5-methoxypyrimidin-2-yl)hexanamide (18.4 g, 84%) as a colorless solid.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting residue was azeotroped with toluene
  7. customThe resulting residue was recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-63fc04445c1c47d6b6618284a3abf5cf
Source dataset
uspto-grants-2010_02
Patent number
US07659271B2

Reaction notes

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