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

HRID 2404006Notes

Reaction equation

HRID 2404006 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]>O1CCCC1>[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 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (5.0 g, 21.5 mmol) and 29% methylamine (5.75 g, 53.72 mmol, methanol (MeOH) solution) in tetrahydrofuran (THF) (100 mL) was stirred at room temperature for 2 hours. The reaction mixture was then concentrated, followed by the addition of sodium bicarbonate (NaHCO3) (aq., 20 mL), and the resulting solution was extracted with ethyl acetate (EtOAc) (3×50 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated to afford ethyl 4-(methylamino)-2-(methylthio)pyrimidine-5-carboxylate (4.68 g, 96%) as a yellowish solid. MS (ES+) C9H13N3O2S requires: 227. found: 228 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additionfollowed by the addition of sodium bicarbonate (NaHCO3) (aq., 20 mL)
  3. extractionthe resulting solution was extracted with ethyl acetate (EtOAc) (3×50 mL)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5333483a207e46969f56da9c0c4f11dd
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

Loading…