Diisopropylethylamine → N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl)pyrimidine-2,4-diamine

HRID 475176

Reaktionsgleichung

Reaktionsgleichung von HRID 475176
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:13][N:12]=[C:11]([CH:14]3[CH2:16][CH2:15]3)[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[N:23]1[C:27]2[CH:28]=[CH:29][C:30]([CH2:32][NH2:33])=[CH:31][C:26]=2[N:25]=[CH:24]1.CCN(C(C)C)C(C)C>CCO>[CH:14]1([C:11]2[NH:12][N:13]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:33][CH2:32][C:30]4[CH:29]=[CH:28][C:27]5[N:23]([CH:18]6[CH2:19][CH2:20][CH2:21][CH2:22][O:17]6)[CH:24]=[N:25][C:26]=5[CH:31]=4)[N:7]=3)[CH:10]=2)[CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 46739877(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamineHCID 178478345HCID 178478345, Verbindung

Produkt 1

HCID 71272519N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl)pyrimidine-2,4-diamineAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A microwave vial was charged with 53 (750 mg, 3.20 mmol), 28 (740 mg, 3.20 mmol), DIPEA (2.0 mL) and EtOH (10.0 mL), sealed and heated at 120° C. for 18 h. The reaction mixture was concentrated in vacuo and purified by SiO2 chromatography eluting with DCM:MeOH (8:1) to afford 1.12 g (81%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl)pyrimidine-2,4-diamine (32) as white solid: MS (ESI) m/z=431.2 [M+1]+.

Aufarbeitung

  1. customsealed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by SiO2 chromatography
  4. washeluting with DCM:MeOH (8:1)

Quellen und Nachweise

ORD-Eintrag
ord-7b125c97ba6a484ba405f841c5d59e78
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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