Potassium Carbonate → 4-(2-Chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl)-3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 1945667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1945667
Br[CH2:2][C:3]1[N:4]([CH3:19])[C:5]2[C:10]([N:11]=1)=[C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[N:8]=[C:7]([Cl:18])[N:6]=2.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][NH:30][C:29]([CH3:34])([CH3:33])[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH2:2][C:3]2[N:4]([CH3:19])[C:5]3[C:10]([N:11]=2)=[C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:8]=[C:7]([Cl:18])[N:6]=3)[C:29]([CH3:34])([CH3:33])[CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 227103871-Boc-3,3-dimethylpiperazineHCID 596034814-(8-(bromomethyl)-2-chloro-9-methyl-9H-purin-6-yl)morpholine

Produkt 1

HCID 596057974-(2-Chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl)-3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl esterAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 8-bromomethyl-2-chloro-9-methyl-6-morpholin-4-yl-9H-purine (400 mg, 1.16 mmol), 3,3-dimethylpiperazine-1-carboxylic acid tert-butyl ester (250 mg, 1.17 mmol) and K2CO3 (176 mg, 1.28 mmol) in DMF (20 mL) was allowed to stir at r.t. for 16 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) affording the title compound (150 mg, 27%). 1H NMR (CDCl3, 400 MHz): δ 4.26 (4 H, brd s), 3.82-3.80 (9 H, m), 3.33 (2 H, brd s), 3.22 (2 H, brd s), 2.42-2.35 (2 H, m), 1.45 (9 H, s), 1.15 (6 H, s).

Aufarbeitung

  1. washwas washed with MeOH
  2. washthe product eluted with 2M NH3/MeOH
  3. customThe resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%)

Quellen und Nachweise

ORD-Eintrag
ord-4b4d772a4b1341d3961b054fafb30eda
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394796B2

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