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

HRID 32533

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

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%);

Workup

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

Sources & evidence

ORD record: ord-997f413299d9486e842b4c251643a252
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427616B2

Linked notes

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