4,4'-(6-Chloropyrimidine-2,4-diyl)dimorpholine → 3-(2,6-Dimorpholinopyrimidin-4-yl)-4-methylaniline

HRID 594056

Reaktionsgleichung

Reaktionsgleichung von HRID 594056
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:3]=1.[CH3:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=1B1OC(C)(C)C(C)(C)O1>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[O:11]1[CH2:12][CH2:13][N:8]([C:6]2[N:7]=[C:2]([C:22]3[CH:23]=[C:24]([CH:26]=[CH:27][C:21]=3[CH3:20])[NH2:25])[CH:3]=[C:4]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:5]=2)[CH2:9][CH2:10]1

Komponenten

6

Edukt 2

HCID 6863344,4'-(6-Chloropyrimidine-2,4-diyl)dimorpholineHCID 160860894-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Produkt 1

HCID 904083603-(2,6-Dimorpholinopyrimidin-4-yl)-4-methylanilineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 4,4′-(6-chloropyrimidine-2,4-diyl)dimorpholine (1.0 equiv.) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.5 equiv.) in DME and 2M sodium carbonate (3:1, 0.2 M) was added PdCl2(dppf)-DCM adduct (0.100 equiv.) in a microwave vial equipped with a stir bar. The reaction was heated to 120° C. for 20 min in the microwave. The reaction mixture qas quenched with water and the aqueous layer was separated and extracted with EtOAc (×3). The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The material was purified via silica gel column chromatography eluting with 100% DCM to 10% MeOH/DCM to afford 3-(2,6-dimorpholinopyrimidin-4-yl)-4-methylaniline in 96% yield. LCMS (m/z) (M+H)=356.2, Rt=0.44 min.

Aufarbeitung

  1. customvial equipped with a stir bar
  2. customThe reaction mixture qas quenched with water
  3. customthe aqueous layer was separated
  4. extractionextracted with EtOAc (×3)
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe material was purified via silica gel column chromatography
  9. washeluting with 100% DCM to 10% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-1709db82e8004ff6a5843968a7288ae2
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242969B2

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