Cesium carbonate → Racemic tert-butyl 4-(2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate

HRID 80788

Reaktionsgleichung

Reaktionsgleichung von HRID 80788
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:10]=[C:11]([N:19]2[C@H:24]([CH3:25])[CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@@H:21]([CH3:33])[CH2:20]2)[C:12]2[CH2:18][NH:17][CH2:16][CH2:15][C:13]=2[N:14]=1.FC(F)(F)S(O[C:40]1[CH:45]=[C:44]([CH:46]([CH3:48])[CH3:47])[CH:43]=[CH:42][C:41]=1[CH3:49])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:10]=[C:11]([N:19]2[C@H:24]([CH3:25])[CH2:23][N:22]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[C@@H:21]([CH3:33])[CH2:20]2)[C:12]2[CH2:18][N:17]([C:40]3[CH:45]=[C:44]([CH:46]([CH3:48])[CH3:47])[CH:43]=[CH:42][C:41]=3[CH3:49])[CH2:16][CH2:15][C:13]=2[N:14]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 130964092-Methyl-5-(propan-2-yl)phenyl trifluoromethanesulfonateHCID 89685949Racemic tert-butyl 4-(2-(2,6-dimethylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate

Produkt 1

HCID 71244713Racemic tert-butyl 4-(2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of racemic tert-butyl 4-(2-(2,6-dimethylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate (0.187 g, 0.414 mmol) in THF (4 mL) was added 5-isopropyl-2-methylphenyl trifluoromethanesulfonate (0.175 g, 0.620 mmol) prepared as described in Example 15, Cs2CO3 (0.404 g, 1.24 mmol) and chloro(2-dicyclohexylphosphino-2′-4′-6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II)-methyl-t-butylether adduct (0.046 mg, 0.062 mmol). The reaction was purged with argon and was heated at 130° C. for 3 h in a microwave reactor. The mixture was then concentrated and the residue was purified via FCC (10-35% EtOAc/heptane) to give racemic tert-butyl 4-(2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate. MS (ESI+) m/z 584.4 (M+H)+.

Aufarbeitung

  1. customprepared
  2. customThe reaction was purged with argon
  3. concentrationThe mixture was then concentrated
  4. customthe residue was purified via FCC (10-35% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-47587ac33dcb42ddb0160b29b6960e85
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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