Water → 2-{(R)-3-[4-(2-tert-Butyl-6-cyclobutylpyrimidin-4-yl)-piperazin-1-yl]-2-methylpropoxy}-4-benzoyloxypyrimidin

HRID 219753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219753
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]([CH3:21])[CH2:19][OH:20])[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CS([C:35]1[N:40]=[C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:38]=[CH:37][N:36]=1)(=O)=O.[OH2:49]>O1CCCC1>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][C@@H:18]([CH3:21])[CH2:19][O:20][C:35]3[N:40]=[C:39]([O:41][C:42](=[O:49])[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:38]=[CH:37][N:36]=3)[CH2:15][CH2:16]2)[CH:8]=[C:7]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 113575332-Methylsulfonyl-4-benzyloxy-pyrimidineHCID 69025424(R)-3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-2-methyl-propan-1-olHCID 178418339Butyllithium

Produkt 1

HCID 690262242-{(R)-3-[4-(2-tert-Butyl-6-cyclobutylpyrimidin-4-yl)-piperazin-1-yl]-2-methylpropoxy}-4-benzoyloxypyrimidin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

1.05 g of (R)-3-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-2-methyl-propan-1-ol (3.02 mmol) were dissolved in 8 ml of tetrahydrofuran. At 0° C., 1.71 ml (3.37 mmol) of n-butyllithium (2 M in pentane) were added within 15 minutes. 0.85 g of 2-methylsulfonyl-4-benzyloxy-pyrimidine (3.21 mmol), dissolved in 5 ml of tetrahydrofurane, were added. Stirring continued for 16 h at room temperature. By cooling with, 2 ml of water were added. The obtained mixture was poured into 15 ml of water and extracted three times with 15 ml of diethyl ether each. The organic layers were combined, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified via silica gel chromatography with dichloromethane, dichloromethane/ethyl acetate 9:1, and dichlormethane/ethyl acetate 3:2 to yield 0.83 g of the product.

Aufarbeitung

  1. additionwere added
  2. additionwere added
  3. extractionextracted three times with 15 ml of diethyl ether each
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified via silica gel chromatography with dichloromethane, dichloromethane/ethyl acetate 9:1, and dichlormethane/ethyl acetate 3:2

Quellen und Nachweise

ORD-Eintrag
ord-00ac25f94b0e43e1a6cf2a87cf0a35d2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202868B2

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