1-methyl-1H-1,3-benzodiazole-2-carbaldehyde → (+/-)-6-[1-Hydroxy-1-(1-methyl-1H-benzimidazol-2-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 379569

Reaktionsgleichung

Reaktionsgleichung von HRID 379569
C([N-]C(C)C)(C)C.[Li+].[CH3:9][N:10]1[C:15](=[O:16])[C:14]2[CH:17]=[CH:18][S:19][C:13]=2[N:12]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:11]1=[O:24].[CH3:25][N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[CH:35]=[O:36]>O1CCCC1>[OH:36][CH:35]([C:18]1[S:19][C:13]2[N:12]([CH2:20][CH:21]([CH3:22])[CH3:23])[C:11](=[O:24])[N:10]([CH3:9])[C:15](=[O:16])[C:14]=2[CH:17]=1)[C:27]1[N:26]([CH3:25])[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=1

Komponenten

5

Edukt 3

HCID 7620841-methyl-1H-1,3-benzodiazole-2-carbaldehydeHCID 2724682Lithium diisopropylamideHCID 52825273-Methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 9930755(+/-)-6-[1-Hydroxy-1-(1-methyl-1H-benzimidazol-2-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneAusbeute 15,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of lithium diisopropylamide (3.15 mmol) in anhydrous tetrahydrofuran (5 ml) was added to a solution of 3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (500 mg) in anhydrous tetrahydrofuran (20 ml) at −78° C. After 10 minutes, 1-methylbenzimidazole-2-carboxaldehyde (600 mg) was added and the resultant solution kept at −78° C. for 1 hour. The reaction mixture was allowed to warm to ambient temperature and quenched with saturated sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate and washed with saturated sodium hydrogen carbonate and then brine, then dried over a mixture of magnesium sulfate and silica, filtered, and evaporated. Purification by HPLC over silica eluting with an isohexane:ethyl acetate gradient (4:1 to 0:1) gave the title compound (0.13 g).

Aufarbeitung

  1. customquenched with saturated sodium hydrogen carbonate solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate
  4. dry with materialbrine, then dried over a mixture of magnesium sulfate and silica
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by HPLC over silica eluting with an isohexane

Quellen und Nachweise

ORD-Eintrag
ord-a42dadee039c4c8cab9e92fadd8430e2
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300334B1

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