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

HRID 53626

Reaction equation

HRID 53626 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].[CH2:15]([N:17](CC)CC)C.CN>O1CCCC1.CCCCCC>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:17][CH3:15])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 295697Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylateYield 81%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (18.66 g, 80.4 mmol) in 260 mL of tetrahydrofuran was added triethylamine (34 mL, 244 mmol), followed by 30 mL of a 40% aqueous solution of methylamine. The solution was stirred for 30 minutes at 25° C. then concentrated in vacuo and partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to provide a white solid. The solid was suspended in hexane and filtered to provide 14.70 g (81%) of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester, mp 91°-93° C.

Workup

  1. concentrationthen concentrated in vacuo
  2. custompartitioned between chloroform and saturated aqueous sodium bicarbonate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a white solid
  8. filtrationfiltered

Sources & evidence

ORD record
ord-b68eeee6024948cfad0d45fea499ee21
Source dataset
uspto-grants-1997_04
Patent number
US05620981

Linked notes

Loading…