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

HRID 1666276노트

반응식

HRID 1666276 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a3d24f5b153949e7b269dd15552afc46
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044062B2

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