Methylamine → 2-chloro-N-methyl-5-nitropyrimidin-4-amine

HRID 29818

反応式

HRID 29818 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][NH2:13]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:13][CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

参加物

4

反応物 2

HCID 6329MethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

生成物 1

HCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amine収率 99.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2,4-dichloro-5-nitropyrimidine (7.26 g, 37.4 mmol) in THF (100 ml) is cooled to −78° C. A solution of methyl amine (8 M in methanol, 9.35 mL, 74.8 mmol) is added dropwise. The mixture is allowed to warm to room temperature, and concentrated. The residue is partitioned between ethyl acetate and water. The layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated to afford the title product (7.0 g). (Note: the product contains 5% regio-isomer, 4-chloro-2-(methylamino)-5-nitropyrimidine). The residue is used in the next step without further purification.

後処理

  1. concentrationconcentrated
  2. customThe residue is partitioned between ethyl acetate and water
  3. customThe layer is separated
  4. extractionthe aqueous layer is extracted with ethyl acetate
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-83d91350d3d04fa4bc5182a219334930
出典データセット
uspto-grants-2008_09
特許番号
US07423038B2

関連ノート

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