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

HRID 32533

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

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

temperaturere-cooled to 0° C
customAfter evaporation of the solvents
filtrationthe solid residue was collected with water by filtration
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

反応式

参加物

反応物 5

生成物 1

試薬・触媒・溶媒 3

反応条件

実験手順

後処理

出典と根拠

関連ノート