Methyl iodide → Methyl 5-((tert-butoxycarbonyl)(methyl)amino)pyrimidine-2-carboxylate

HRID 1526616Notes

Reaction equation

HRID 1526616 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[N:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH3:19])[C:9]1[CH:14]=[N:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 67980903Methyl 5-((tert-butoxycarbonyl)amino)pyrimidine-2-carboxylate

Product 1

HCID 90389408Methyl 5-((tert-butoxycarbonyl)(methyl)amino)pyrimidine-2-carboxylateYield 84.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 5-((tert-butoxycarbonyl)amino)pyrimidine-2-carboxylate (1.31 g, 5.16 mmol) in DMF (13 mL) was treated with cesium carbonate (2.19 g, 6.71 mmol) followed by iodomethane (0.64 mL, 10.32 mmol). The resulting suspension was stirred at ambient temperature for 5 h. The suspension was diluted with DCM (50 mL), filtered, concentrated, and purified by flash chromatography on silica gel eluting with a gradient of 0 to 40% EtOAc in DCM to give methyl 5-((tert-butoxycarbonyl)(methyl)amino)pyrimidine-2-carboxylate (1.16 g, 84% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.91 (s, 2H), 4.07 (s, 3H), 3.38 (s, 3H), 1.52 (s, 9H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified by flash chromatography on silica gel eluting with a gradient of 0 to 40% EtOAc in DCM

Sources & evidence

ORD record
ord-c370875d86984e9d9572fbada6318bbb
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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