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

HRID 1526616

반응식

HRID 1526616 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-c370875d86984e9d9572fbada6318bbb
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085576B2

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