Ethyl ethoxyacetate → 2-Butylsulfanyl-6-ethoxy-8,8a-dihydro-4ahpyrido[2,3-d]pyrimidin-7-one

HRID 459906

反応式

HRID 459906 の反応式
[NH2:1][CH:2]1[CH:7]([CH:8]=O)[CH:6]=[N:5][C:4]([S:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:3]1.[CH2:15]([O:17][CH2:18][C:19](OCC)=[O:20])[CH3:16].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[CH2:11]([S:10][C:4]1[N:5]=[CH:6][CH:7]2[CH:8]=[C:18]([O:17][CH2:15][CH3:16])[C:19](=[O:20])[NH:1][CH:2]2[N:3]=1)[CH2:12][CH2:13][CH3:14]

参加物

5

反応物 3

HCID 69955Ethyl ethoxyacetate2 回HCID 21956055HCID 21956055、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 219560512-Butylsulfanyl-6-ethoxy-8,8a-dihydro-4ahpyrido[2,3-d]pyrimidin-7-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

4-Amino-2-butylsulfanyl-4,5-dihydro-pyrimidine-5-carbaldehyde (3 g, 14.2 mmol, furnished by scaleup) and ethyl ethoxyacetate (2.34 g, 2.4 ml, 17.75 mmol) were stirred in 80 ml toluene at 0°-5° C. under nitrogen. Potassium t-butoxide (1.75 g, 15.6 mmol) was added gradually. The mixture was stirred to ambient temperature, and then to 65° C. for 48 hours. An additional 20 ml of toluene and 2.4 ml ethyl ethoxyacetate were added and the reaction was maintained at 65° C. over the weekend. The reaction mixture was concentrated in vacuo and triturated with EtOAc to remove the remaining starting aldehyde. The remaining solid was further triturated with chloroform to remove additional impurities. 3.66 g of 2-Butylsulfanyl-6-ethoxy-8,8a-dihydro-4aHpyrido[2,3-d]pyrimidin-7-one (1A) of a purity greater than 80% as judged by MS/HPLC and NMR was collected.

後処理

  1. temperaturethe reaction was maintained at 65° C. over the weekend
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customtriturated with EtOAc
  4. customto remove the remaining starting aldehyde
  5. customThe remaining solid was further triturated with chloroform
  6. customto remove additional impurities
  7. customwas collected

出典と根拠

ORDレコード
ord-6cd10b64cb5b47d8a8a9f9930b4e7750
出典データセット
uspto-grants-2007_03
特許番号
US07196097B2

関連ノート

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