Trimethyl orthoformate → HCID 86710193, Verbindung

HRID 2284431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2284431
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][C:6]=2[N:7]=1.[OH:20][CH:21]([CH3:30])[C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23].C(OC)(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.ClCCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[CH:10][C:9]([CH2:12][N:27]3[CH2:26][CH2:25][N:24]([C:22](=[O:23])[CH:21]([OH:20])[CH3:30])[CH2:29][CH2:28]3)=[CH:8][C:6]=2[N:7]=1

Komponenten

7

Edukt 4

HCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 13460159Piperazine, 1-(2-hydroxy-1-oxopropyl)- (9CI)HCID 86710192HCID 86710192, Verbindung

Produkt 1

HCID 86710193HCID 86710193, VerbindungAusbeute 35,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 50 mL round bottom flask, 2-chloro-4-morpholinopyrido[3,2-d]pyrimidine-7-carbaldehyde (0.3 g, 0.0010 mol) and 1,2-dichloroethane (20 mL) were added. To the reaction flask, 2-hydroxy-1-(piperazin-1-yl)propan-1-one (0.204 g, 0.0013 mol) and trimethyl orthoformate (0.228 g, 0.0030 mol) were added and the reaction mixture stirred at room temperature for 12 hours. To the reaction mixture, sodium triacetoxyborohydride (g, 0.683 0.0020 mol) was added and stirred at room temperature for 3 hours. The reaction mixture was diluted with DCM, washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform) to provide the title compound (0.15 g, 33%). 1H NMR (300 MHz, CDCl3): δ 8.62 (d, J=1.8 Hz, 1H), 7.86 (d, J=1.2 Hz, 1H), 4.72 (br s, 4H), 3.84 (t, J=9.0 Hz, 4H), 3.65 (s, 2H), 3.60-3.52 (m, 1H), 3.41 (d, J=2.7 Hz, 1H), 3.23 (s, 4H), 2.46 (d, J=3.0 Hz, 4H), 1.27 (d, J=6.6 Hz, 3H): LC-MS (ESI): Calculated mass. 420.1, Observed mass [M+H]+: 421.1 (RT=0.24 min).

Aufarbeitung

  1. stirringstirred at room temperature for 3 hours
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customto provide the crude product
  6. customThe crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-4bda41f29c4441d5ba2dd55927fcb93f
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145411B2

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