Ethanol → 2-{2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-1-methyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one

HRID 474871

Reaktionsgleichung

Reaktionsgleichung von HRID 474871
CS[C:3]1[NH:4][CH:5]=[C:6]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[C:7](=[O:9])[N:8]=1.[Cl:17][C:18]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH2:31])=[CH:25][CH:24]=2)=[CH:20][C:19]=1[C:34]([F:37])([F:36])[F:35].[CH2:38](O)C>>[Cl:17][C:18]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH:31][C:3]3[N:4]([CH3:38])[CH:5]=[C:6]([CH2:10][C:11]4[CH:12]=[N:13][CH:14]=[N:15][CH:16]=4)[C:7](=[O:9])[N:8]=3)=[CH:25][CH:24]=2)=[CH:20][C:19]=1[C:34]([F:35])([F:36])[F:37]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 677755482-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamineHCID 178503543HCID 178503543, Verbindung

Produkt 1

HCID 677757712-{2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-1-methyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

2-Methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (18.6 mg, 0.079 mmol, 1 eq) and 2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamine (39.3 mg, 0.119 mmol, 1.5 eq) were dissolved in dry ethanol (300 μl) and stirred at 125° C. for 48 h. Reaction mixture was evaporated and crude residue was purified via Biotage SP-1 Snap Si 10 g; 15 ml/min in the gradient of MeOH in DCM: 1% for 1 CV then from 1-5% for 20 CV. The appropriate fractions were combined and evaporated in vacuo to give the required product which was not pure enough and it was sent to HPLC/MS Purification. After HPLC/MS purification combined fractions of desired product were collected and put on lyophilisation to obtain 2-{2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-1-methyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (0.0095 mmol; yield: 10%, HPLC-MS/UV: [M+H]+=516.93; rt: 11.49 min; purity: 96%). 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.82 (t, J=8.17 Hz, 2H), 3.40-3.52 (m, 4H), 6.92 (m, 1H), 7.05 (d, J=8.59 Hz, 2H), 7.22 (dd, J=9.11, J=2.72, 1H), 7.28 (d, J=8.29, 2H), 7.38-7.44 (m, 2H), 7.67 (d, J=8.84, 1H), 8.67 (s, 2H), 8.97 (s, 1H)

Aufarbeitung

  1. customReaction mixture
  2. customwas evaporated
  3. customcrude residue was purified via Biotage SP-1 Snap Si 10 g
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7028e3414321481dbef07f9454f93d76
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637536B2

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