Dibutyltin oxide → HCID 178525388, Verbindung

HRID 870588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870588
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[N:12]=[CH:13][C:14]2[CH2:20][N:19]([C:21]([O:23][CH2:24][CH2:25][CH2:26][C:27]#[N:28])=[O:22])[CH2:18][CH2:17][C:15]=2[N:16]=1.[N:29]([Si](C)(C)C)=[N+:30]=[N-:31].C([Sn](CCCC)=O)CCC>C1(C)C=CC=CC=1.ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[N:12]=[CH:13][C:14]2[CH2:20][N:19]([C:21]([O:23][CH2:24][CH2:25][CH2:26][C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[O:22])[CH2:18][CH2:17][C:15]=2[N:16]=1

Komponenten

6

Edukt 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 867265503-cyanopropyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Produkt 1

HCID 178525388HCID 178525388, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Heat a solution of 3-cyanopropyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.24 g; 1.0 equiv; 0.64 mmoles), azidotrimethylsilane (0.85 mL; 10 equiv; 6.38 mmoles) and dibutyloxostannane (0.040 g; 0.25 equiv; 0.16 mmoles) in toluene (5 mL) to 100° C. for 24 hours, then cool to ambient temperature and concentrate. Purify the crude material by reverse phase chromatography to afford impure product. Dissolve the impure product in 50 mL dichloromethane and wash with saturated sodium bicarbonate, and further extract the aqueous layer 2× dichloromethane. Dry the combined organic extracts over sodium sulfate, filter, and concentrate to afford 3-(1H-tetrazol-5-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.110 g; 41%) as a yellow solid: MS (m/z): 421 (M+1).

Aufarbeitung

  1. concentrationconcentrate
  2. customPurify the crude material by reverse phase chromatography
  3. customto afford impure product
  4. washwash with saturated sodium bicarbonate
  5. extractionfurther extract the aqueous layer 2× dichloromethane
  6. dry with materialDry the combined organic extracts over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-939d1667a7594c01ae680122bd6e27b1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969555B2

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