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

HRID 1696438Notes

Reaction equation

HRID 1696438 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].[CH3:15][NH2:16]>CCO>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:16][CH3:15])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]

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 39,797.102%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4-chloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester (42 g, 0.181 mol) in EtOH (400 mL) was added MeNH2 (12.3 g, 0.398 mmol) in EtOH (100 mL) at 0° C. and the mixture stirred for 3 h. The mixture was concentrated to remove most of the solvent and then partitioned between H2O (200 mL) and CH2Cl2 (500 mL). The organic layer was washed with brine, dried and concentrated to give 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester as a white solid (36.0 g, 88% yield). 1H NMR (300 MHz, CDCl3): δ 8.59 (s, 1H), 8.18 (brs, 1H), 4.31 (q, J=7.2 Hz, 2H), 3.05 (d, J=4.8 Hz, 3H), 2.52 (s, 3H), 1.34 (t, J=7.2 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove most of the solvent
  3. custompartitioned between H2O (200 mL) and CH2Cl2 (500 mL)
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6f25d8d848ae4419b99d6fa466332ecd
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

Loading…