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N-Methoxy-N-methylbenzamide → 1-[4-(Methylthio)thieno[3,2-d]pyrimidin-6-yl]-2-phenylethane-1,2-dione 1-oxime

HRID 32533
ノート
印刷プレビュー

反応式

HRID 32533 の反応式
CC1SC2C(SC)=NC=NC=2C=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C[O:24][N:25](C)C(=O)C1C=CC=CC=1.[CH3:35][S:36][C:37]1[C:38]2[S:45][C:44]([CH2:46][C:47]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[O:48])=[CH:43][C:39]=2[N:40]=[CH:41][N:42]=1.N([O-])=O.[Na+]>C1COCC1.O.C(O)(=O)C>[CH3:35][S:36][C:37]1[C:38]2[S:45][C:44]([C:46](=[N:25][OH:24])[C:47]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[O:48])=[CH:43][C:39]=2[N:40]=[CH:41][N:42]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 569575N-Methoxy-N-methylbenzamideHCID 2733832Lithium hexamethyldisilazaneHCID 179658316-Methyl-4-(methylthio)thieno[3,2-d]pyrimidineHCID 179658672-[4-(Methylthio)thieno[3,2-d]pyrimidin-6-yl]-1-phenylethanoneHCID 23668193Sodium Nitrite

生成物 1

HCID 136337744
1-[4-(Methylthio)thieno[3,2-d]pyrimidin-6-yl]-2-phenylethane-1,2-dione 1-oxime
収率 86%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

6-Methyl-4-(methylthio)thieno[3,2-d]pyrimidine, (intermediate 22) (665 mg) was dissolved in THF (10 mL) and added slowly, over 15 minutes, to a stirred solution of LHMDS in THF (1M, 3.39 mL) at −78° C. After 10 minutes, N-methoxy-N-methylbenzamide (616 mg) was added and the reaction mixture warmed to 0° C. After 2 hours at 0° C. the resultant solution of 2-[4-(methylthio)thieno[3,2-d]pyrimidin-6-yl]-1-phenylethanone was acidified with acetic acid (10 mL), diluted with water (10 mL) and re-cooled to 0° C. Sodium nitrite (280 mg) was added and the mixture was stirred overnight. After evaporation of the solvents, the solid residue was collected with water by filtration, and dried to give the title compound as a brown solid (959 mg, 86%);

後処理

  1. temperaturere-cooled to 0° C
  2. customAfter evaporation of the solvents
  3. filtrationthe solid residue was collected with water by filtration
  4. customdried

出典と根拠

ORDレコード
ord-997f413299d9486e842b4c251643a252
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07427616B2

反応ノート

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