Sodium Carbonate → Racemic tert-Butyl 4-(6-benzyl-2-(2,6-dimethylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate

HRID 80786

Reaktionsgleichung

Reaktionsgleichung von HRID 80786
[CH2:1]([N:8]1[CH2:33][CH2:32][C:11]2[N:12]=[C:13](Cl)[N:14]=[C:15]([N:16]3[C@H:21]([CH3:22])[CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:18]([CH3:30])[CH2:17]3)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:36]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH2:33][CH2:32][C:11]2[N:12]=[C:13]([C:36]3[C:37]([CH3:41])=[CH:38][CH:39]=[CH:40][C:35]=3[CH3:34])[N:14]=[C:15]([N:16]3[C@H:21]([CH3:22])[CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:18]([CH3:30])[CH2:17]3)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 5833222,6-Dimethylphenylboronic acidHCID 89400111Racemic tert-butyl 4-(6-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate

Produkt 1

HCID 71244696Racemic tert-Butyl 4-(6-benzyl-2-(2,6-dimethylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of racemic tert-butyl 4-(6-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate (0.54 g, 1.14 mmol) in DME (9 mL) was added 2,6-dimethylphenylboronic acid (0.257 g, 1.72 mmol), Pd(Ph3P)4 (0.198 g, 0.172 mmol) and a 2 M aq solution of sodium carbonate (1.9 mL). The reaction was heated at 140° C. in a microwave reactor for 1.75 h. The reaction was filtered and diluted with EtOAc and brine. The organic layer was separated and then dried (Na2SO4), filtered and concentrated. The residue was then purified by FCC (55-80% EtOAc/heptane) to give the title compound. MS (ESI+) m/z 542.5 (M+H)+.

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. additiondiluted with EtOAc and brine
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was then purified by FCC (55-80% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-299759047ca24b6ab110fc1ebad8cdad
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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