4-Aminopyridine → 2-(biphenyl-4-ylmethyl)-7-isobutyl-5-methyl-3-(pyridin-4-ylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81413

Reaktionsgleichung

[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16](I)=[C:15]3[C:10]([N:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12](=[O:20])[N:13]([CH3:19])[C:14]3=[O:18])=[N:9]2)=[CH:3][CH:2]=1.[N:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(O[K])(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]([NH:37][C:34]3[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=3)=[C:15]3[C:10]([N:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12](=[O:20])[N:13]([CH3:19])[C:14]3=[O:18])=[N:9]2)=[CH:3][CH:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

2-(biphenyl-4-ylmethyl)-3-iodo-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (13.6 mg, 0.026 mmol) is dissolved in anhydrous and degassed THF, and then 4-pyridyl amine (13 mg, 0.132 mmol), Pd2(dba)3 (12 mg, 0.013 mmol) and Xantphos (9 mg, 0.016 mmol) are added, followed by tBuOK (7.5 mg, 0.065 mmol). The reaction mixture is heated in microwave at 150° C. for 40 minutes. After cooling and filtration, the filtrate is purified by a semi-preparative HPLC to give product. MS (ESI) m/z 481.2 [M+H]+

Aufarbeitung

customdegassed THF
temperatureAfter cooling
filtrationfiltration
customthe filtrate is purified by a semi-preparative HPLC
customto give product

Quellen und Nachweise

ORD-Eintrag: ord-5074a99527b24e97a904d6d5ca7f3a40
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846693B2

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