Methylamine → Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate

HRID 1930392Notes

Reaction equation

HRID 1930392 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[CH3:15][NH2:16]>CCO>[CH3:15][NH:16][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 295697Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (42 g, 181 mmol) in EtOH (400 mL) was treated with a solution of methylamine (12.3 g, 397 mmol) in EtOH (100 mL) at 0° C. and the mixture was stirred for 3 h. The mixture was concentrated and then partitioned between H2O (200 mL) and CH2Cl2 (500 mL). The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo to give ethyl 4-(methylamino)-2-(methylthio)pyrimidine-5-carboxylate as a white solid (36.0 g, 88% yield). 1H NMR (300 MHz, CDCl3): 8.59 (s, 1 H), 8.18 (br s, 1 H), 4.31 (q, J=7.2 Hz, 2 H), 3.05 (d, J=4.8 Hz, 3 H), 2.52 (s, 3 H), 1.34 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 228.1 (M+H+).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between H2O (200 mL) and CH2Cl2 (500 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-011df84c22ec4cf2acd91d55b269ebea
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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