Tetrahydrofuran → 1-(4-Chloro-3-(2-(2-(dimethylamino)ethylamino)-8-methoxy-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(3-chloro-4-methoxyphenyl)urea

HRID 1517247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517247
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:27])=[C:6]([C:8]2[C:23](=[O:24])[N:22]([O:25][CH3:26])[C:11]3[N:12]=[C:13]([NH:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[N:14]=[CH:15][C:10]=3[CH:9]=2)[CH:7]=1.[Cl:28][C:29]1[CH:34]=[C:33]([N:35]=[C:36]=[O:37])[CH:32]=[CH:31][C:30]=1[O:38][CH3:39].C1COCC1>>[Cl:27][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:36]([NH:35][C:33]2[CH:32]=[CH:31][C:30]([O:38][CH3:39])=[C:29]([Cl:28])[CH:34]=2)=[O:37])=[CH:7][C:6]=1[C:8]1[C:23](=[O:24])[N:22]([O:25][CH3:26])[C:11]2[N:12]=[C:13]([NH:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[N:14]=[CH:15][C:10]=2[CH:9]=1

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 1199472-Chloro-4-isocyanatoanisoleHCID 584783586-(5-amino-2-chlorophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one

Produkt 1

HCID 444633121-(4-Chloro-3-(2-(2-(dimethylamino)ethylamino)-8-methoxy-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(3-chloro-4-methoxyphenyl)ureaAusbeute 56 %

Versuchsvorschrift

In a 3 ml vial equipped with a small triangular magnetic stirring bar was placed 6-(5-amino-2-chlorophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin -7(8H)-one (165 μmol). A solution of 2-chloro-4-isocyanato-1-methoxybenzene in THF (2 mL, 129 mmol) was added, and the mixture was stirred at room temperature over night. The solvent was allowed to evaporate over night, and the remaining solid was dissolved in DMSO, transferred to maximum recovery HPLC vials and purified by prep. HPLC-MS. The collected fractions were transferred to centrifuge vials and lyophilized, giving 1-(4-chloro-3-(2-(2-(dimethylamino)ethylamino)-8-methoxy-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl) -3-(3-chloro-4-methoxyphenyl)urea as a solid (56%).

Aufarbeitung

  1. customIn a 3 ml vial equipped with a small triangular magnetic stirring bar
  2. customto evaporate over night
  3. dissolutionthe remaining solid was dissolved in DMSO
  4. custompurified by prep

Quellen und Nachweise

ORD-Eintrag
ord-7cdae29fbacb462c93795ea4133e88ad
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232283B2

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