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

HRID 1526616

反応式

HRID 1526616 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c370875d86984e9d9572fbada6318bbb
出典データセット
uspto-grants-2015_07
特許番号
US09085576B2

関連ノート

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