Methylamine → Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate
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
Product 1
Reagents, catalysts & solvents 2
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
- concentrationthen concentrated in vacuo
- custompartitioned between chloroform and saturated aqueous sodium bicarbonate
- washThe organic layer was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto provide a white solid
- filtrationfiltered
Sources & evidence
- ORD record
- ord-593adeb78ad54af0a1dc7e4266a066bd
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05945422
Reaction notes
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