تفاعل #655099

ord-998a81851c3e4775950226110ecde8a5

معادلة التفاعل

O
Water
N#Cc1ccccc1C=O
o-cyanobenzaldehyde
CC(C)Cn1c(=O)n(C)c(=O)c2ccsc21
3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidin-2,4(1H,3H)-dione
CC(C)[N-]C(C)C.[Li+]
lithium diisopropylamide
CC(C)Cn1c(=O)n(C)c(=O)c2cc(C3OC(=N)c4ccccc43)sc21
title compound
CC(C)Cn1c(=O)n(C)c(=O)c2cc(C3OC(=N)c4ccccc43)sc21
6-(3-Imino-1,3-dihydro-benzo[c]furan-1-yl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H, 3H)-dione

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONadded
  2. 2
    استخلاصThe mixture was extracted with ethyl acetate
  3. 3
    أخرىThe organic layer was separated
  4. 4
    تجفيفdried over magnesium sulfate
  5. 5
    تركيزconcentrated in vacuo
  6. 6
    أخرىpurified by normal phase HPLC

الإجراء التجريبي

To a solution of 3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidin-2,4(1H,3H)-dione (500 mg) in tetrahydrofuran (10 ml) at −78° C. was added lithium diisopropylamide (1M, 3.1 ml). After 5 minutes a solution of o-cyanobenzaldehyde in tetrahydrofuran (2 ml) was added and the reaction was allowed to stir for 2 h. Water (10 ml) was the added and the mixture was allowed to warm to room temperature. The mixture was extracted with ethyl acetate. The organic layer was separated and dried over magnesium sulfate, then concentrated in vacuo and purified by normal phase HPLC to yield the title compound (15 mg).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06180635B2uspto-grants-2001_01