Water → 3-(1,3-Dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

HRID 2201288

Reaktionsgleichung

Reaktionsgleichung von HRID 2201288
[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:14][CH2:15][S:16][C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10](B(O)O)=[C:6]2[C:5](=[O:36])[N:4]([CH3:37])[C:3]1=[O:38].Br[C:40]1[CH:41]=[C:42]([CH:45]=[CH:46][CH:47]=1)[C:43]#[N:44].[OH-].[Ba+2].[OH-].O>C(OC(C)=O)CCC.C(Cl)Cl>[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:14][CH2:15][S:16][C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]([C:40]3[CH:41]=[C:42]([CH:45]=[CH:46][CH:47]=3)[C:43]#[N:44])=[C:6]2[C:5](=[O:36])[N:4]([CH3:37])[C:3]1=[O:38]

Komponenten

7

Edukt 4

HCID 962WaterHCID 233813-BromobenzonitrileHCID 6093286Barium hydroxideHCID 867235221,3-Dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-ylboronic acid2×

Produkt 1

HCID 867235233-(1,3-Dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 31272Butyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension comprising 1,3-dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-ylboronic acid (Intermediate F) (300 mg, 0.571 mmol), 3-bromobenzonitrile (104 mg, 0.571 mmol) and barium hydroxide (196 mg, 1.142 mmol) in n-BuOAc (5710 μL) was treated with Pd-118 (18.61 mg, 0.029 mmol) and the mixture was heated to 80° C. Water (247 μL, 13.70 mmol) was added at 80° C. and the suspension was stirred rapidly for 90 minutes. After cooling to RT, the mixture was allowed to stand at RT overnight. The mixture was diluted with DCM (50 ml) and washed with water (50 ml). The layers were separated and the aqueous portion was extracted with DCM (3×30 ml). The organics were combined and dried over MgSO4, filtered and concentrated. Purification of the crude product by trituration with EtOAc/iso-hexane afforded the title compound;

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. waitto stand at RT overnight
  3. washwashed with water (50 ml)
  4. customThe layers were separated
  5. extractionthe aqueous portion was extracted with DCM (3×30 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the crude product by trituration with EtOAc/iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-4850ca5bab394087b91fa98af5f92589
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359381B2

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