Malononitrile → 8-Ethyl-7-imino-4-methyl-2-(methylthio)-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

HRID 1666276ノート

反応式

HRID 1666276 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:9][C:10]1[C:15]([CH:16]=O)=[C:14]([CH3:18])[N:13]=[C:12]([S:19][CH3:20])[N:11]=1)[CH3:8].[C:21](#[N:25])[CH2:22][C:23]#[N:24]>C(O)C>[CH2:7]([N:9]1[C:10]2[N:11]=[C:12]([S:19][CH3:20])[N:13]=[C:14]([CH3:18])[C:15]=2[CH:16]=[C:22]([C:23]#[N:24])[C:21]1=[NH:25])[CH3:8]

参加物

5

反応物 3

HCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 576069534-(Ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carbaldehyde

生成物 1

HCID 576069898-Ethyl-7-imino-4-methyl-2-(methylthio)-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

Potassium carbonate (0.539 g, 3.90 mmol) was added to a suspension of 4-(ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carbaldehyde (0.413 g, 1.95 mmol) from above, and malononitrile (0.194 g, 2.93 mmol) in absolute ethanol (15.0 mL) and heated to 70° C. After one h, the reaction was allowed to cool to room temperature and concentrated in vacuo. The residue was diluted with ethyl acetate (50 mL) and washed with saturated NaHCO3 (50 mL), and brine. The organic phase was separated and concentrated in vacuo. The residue was precipitated with ethyl acetate and hexanes to give 8-ethyl-7-imino-4-methyl-2-(methylthio)-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile as a brown solid that was used in the subsequent step without further purification.

後処理

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate (50 mL)
  4. washwashed with saturated NaHCO3 (50 mL), and brine
  5. customThe organic phase was separated
  6. concentrationconcentrated in vacuo
  7. customThe residue was precipitated with ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-a3d24f5b153949e7b269dd15552afc46
出典データセット
uspto-grants-2011_10
特許番号
US08044062B2

反応ノート

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