Tetrahydrofuran → Tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(2-methoxypyrimidin-5-ylamino)pyridin-3-yl)methyl)piperazine-1-carboxylate

HRID 1621705

Reaktionsgleichung

Reaktionsgleichung von HRID 1621705
[CH3:1][O:2][C:3]1[CH:47]=[CH:46][C:6]([CH2:7][N:8]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH2:23][N:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]4)[CH:19]=[N:20][C:21]=3F)[N:10]=2)=[CH:5][CH:4]=1.[CH3:48][O:49][C:50]1[N:55]=[CH:54][C:53]([NH2:56])=[CH:52][N:51]=1.O1CCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>>[CH3:1][O:2][C:3]1[CH:47]=[CH:46][C:6]([CH2:7][N:8]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH2:23][N:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]4)[CH:19]=[N:20][C:21]=3[NH:56][C:53]3[CH:52]=[N:51][C:50]([O:49][CH3:48])=[N:55][CH:54]=3)[N:10]=2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 3529042-Methoxypyrimidin-5-amineHCID 2733832Lithium HexamethyldisilazideHCID 60156087Tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-fluoropyridin-3-yl)methyl)piperazine-1-carboxylate

Produkt 1

HCID 59548319Tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(2-methoxypyrimidin-5-ylamino)pyridin-3-yl)methyl)piperazine-1-carboxylateAusbeute 72,2 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-fluoropyridin-3-yl)methyl)piperazine-1-carboxylate (0.500 g, 0.777 mmol) and 2-methoxypyrimidin-5-amine (0.117 g, 0.932 mmol) (ACES PHARMA) in tetrahydrofuran (10 mL, 123 mmol) was stirred at 0° C. and treated dropwise via syringe with lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran; 2.330 mL, 2.330 mmol). The solution was stirred at 0° C. for 1 h. The solution was quenched with water (10 mL) and diluted with water (15 mL) and EtOAc (100 mL). The organic layer was separated and dried over Na2SO4, filtered and concentrated in vacuo to give tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(2-methoxypyrimidin-5-ylamino)pyridin-3-yl)methyl)piperazine-1-carboxylate (0.420 mg, 0.561 mmol, 72% yield). m/z (ESI, +ve ion) 749.4 (M+H)+.

Aufarbeitung

  1. customThe solution was quenched with water (10 mL)
  2. additiondiluted with water (15 mL) and EtOAc (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ae82cceaa51242ca8b9f497e902d4507
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

Verknüpfte Notizen

Wird geladen…