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Potassium Carbonate → 7-(2,2-dimethyl-propyl)-6-(1,4-dioxo-3,4-dihydro-1H-phthalazin-2-ylmethyl)-7H-pyrrolo[2,3-d)pyrimidine-2-carbonitrile

HRID 271608
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 271608
[C:1]([NH:13][NH2:14])(=[O:12])[C:2]1[C:3](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:4](NN)=[O:5].C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23]1[N:33]([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:26]2[N:27]=[C:28]([C:31]#[N:32])[N:29]=[CH:30][C:25]=2[CH:24]=1>CN(C=O)C>[CH3:36][C:35]([CH3:38])([CH3:37])[CH2:34][N:33]1[C:26]2[N:27]=[C:28]([C:31]#[N:32])[N:29]=[CH:30][C:25]=2[CH:24]=[C:23]1[CH2:22][N:14]1[NH:13][C:1](=[O:12])[C:2]2[C:3](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:4]1=[O:5]
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 113128256-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileHCID 11367556Phthalohydrazide

Produkt 1

HCID 689289407-(2,2-dimethyl-propyl)-6-(1,4-dioxo-3,4-dihydro-1H-phthalazin-2-ylmethyl)-7H-pyrrolo[2,3-d)pyrimidine-2-carbonitrileAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of 338 mg (1.3 mmoles) of phthalhydrazide in 20 ml of DMF, 252 mg (1.83 mmoles) of K2CO3 and 400 mg (1.30 mmoles) of 6-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile are added successively and the mixture is stireed for 18 hours at ambient temperature. The reaction mixture is quenched with ice-water and extracted with AcOEt. The combined extracts are washed with H2O, brine and dried over MgSO4. Chromatography on silica gel (eluent: n-Hexane:AcOEt=1:2) give 412 mg of desired 7-(2,2-dimethyl-propyl)-6-(1,4-dioxo-3,4-dihydro-1H-phthalazin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 70% yield. The obtained product is treated with MeJ under the same conditionto give N-methylated compound. To a solution of 295 mg (0.76 mmoles) of 7-(2,2-dimethyl-propyl)-6-(1,4-dioxo-3,4-dihydro-1H-phthalazin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 20 ml of DMF, 0.066 ml (1.06 mmoles) of MeJ and 168 mg (1.22 mmoles) of K2CO3 are added successively and the mixture is stireed for 18 hours at ambient temperature. The reaction mixture is quenched with ice-water and extracted with AcOEt. The combined extracts are washed with H2O, brine and dried over MgSO4. Chromatography on silica gel (eluent: n-Hexane:AcOEt=1:4) give 238 mg of 7-(2,2-Dimethyl-propyl)-6-(3-methyl-1,4dioxo-3,4-dihydro-1H-phthalazin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 78% yield.

Aufarbeitung

  1. customThe reaction mixture is quenched with ice-water
  2. extractionextracted with AcOEt
  3. washThe combined extracts are washed with H2O, brine
  4. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-ce718686ca8e426997a46115680654f5
Quelldatensatz
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07452886B2

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