5-Bromo-2-fluoro-3-pyridinecarboxaldehyde → 6-bromo-N-methylpyrido[2,3-d]pyrimidin-2-amine

HRID 522736ノート

反応式

HRID 522736 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=O)[C:5](F)=[N:6][CH:7]=1.Cl.[CH3:12][NH:13][C:14]([NH2:16])=[NH:15]>C(#N)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[N:15]=[C:14]([NH:13][CH3:12])[N:16]=[CH:9][C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 454801925-Bromo-2-fluoro-3-pyridinecarboxaldehydeHCID 178485118HCID 178485118、化合物

生成物 1

HCID 588291426-bromo-N-methylpyrido[2,3-d]pyrimidin-2-amine収率 24%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
180 °C

実験手順

Treat a solution of 5-bromo-2-fluoropyridine-3-carboxaldehyde (0.50 g, 2.451 mmol) and 1-methylguanidine hydrochloride (0.322 g, 2.94 mmol) in acetonitrile (20 mL) with TEA (0.947 mL, 7.35 mmol) and heat to 180° C. in the microwave for 15 min. Concentrate the mixture to dryness, treat the residue with DCM and wash with H2O, then brine. Dry the organic layer over Na2SO4, concentrate to dryness and purify via silica gel chromatography (20-100% EtOAc/Hexanes) to afford the title compound (140 mg, 24% yield). MS (m/z): 241.0 (M+1).

後処理

  1. concentrationConcentrate the mixture to dryness
  2. additiontreat the residue with DCM
  3. washwash with H2O
  4. dry with materialDry the organic layer over Na2SO4
  5. concentrationconcentrate to dryness
  6. custompurify via silica gel chromatography (20-100% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-340191897e0b49d9b5800485779361fd
出典データセット
uspto-grants-2016_05
特許番号
US09334267B2

反応ノート

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