Diisopropylethylamine → N-[4-Fluoropyrimidin-2-yl]-N-methylglycine, methyl ester

HRID 1871989Notes

Reaction equation

HRID 1871989 reaction equation
F[C:2]1[N:7]=[C:6]([F:8])[CH:5]=[CH:4][N:3]=1.Cl.[CH3:10][O:11][C:12](=[O:16])[CH2:13][NH:14][CH3:15].C(N(CC)C(C)C)(C)C>CCCC(C)C>[F:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:14]([CH3:15])[CH2:13][C:12]([O:11][CH3:10])=[O:16])[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 1377162,4-Difluoropyrimidine

Product 1

HCID 131721952N-[4-Fluoropyrimidin-2-yl]-N-methylglycine, methyl ester

Reagents, catalysts & solvents 1

HCID 78922-MethylpentaneSolvent

Procedure

To a solution of 2,4-difluoropyrimidine (J.Heterocyclic Chem. 1985, 22, 149) (4.48 g) in isohexane (50 ml) at 0° C. was added sarcosine methyl ester hydrochloride (5.39 g) followed by N,N-diisopropylethylamine (13.45 ml). After 5 minutes, the ice bath was removed and the reaction mixture allowed to stir at room temperature for 3 hours. The solvents were evaporated under reduced pressure and the residue purified by chromatography eluting with ethyl acetate/isohexane mixtures. The first and minor component of the mixture to be eluted was the subtitle compound. Yield 0.68 g.

Workup

  1. customthe ice bath was removed
  2. customThe solvents were evaporated under reduced pressure
  3. customthe residue purified by chromatography
  4. washeluting with ethyl acetate/isohexane
  5. washThe first and minor component of the mixture to be eluted

Sources & evidence

ORD record
ord-cce0d260c79748ba8a0254c7f30ce267
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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