Triethylamine → N-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-2-(dimethylamino)acetamide

HRID 2098810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098810
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][NH2:12])=[CH:8][C:6]=2[N:7]=1.CCN(CC)CC.C([O:28][C:29](=O)[CH2:30][N:31]([CH3:33])[CH3:32])C>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:5]2[S:10][C:9]([CH2:11][NH:12][C:29](=[O:28])[CH2:30][N:31]([CH3:33])[CH3:32])=[CH:8][C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 118412Glycine, N,N-dimethyl-, ethyl esterHCID 46180727(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanamine

Produkt 1

HCID 86618441N-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-2-(dimethylamino)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanamine 27 from Example 11 (50 mg, 0.2 mmol) in CH2Cl2 (4 mL) was added Et3N (84 μL, 0.6 mmol) and dimethylglycine ethyl ester (0.3 mmol). The reaction stirred 18-48 h at room temperature before being quenched with water. The aqueous layer was extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated in vacuo to give N-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-2-(dimethylamino)acetamide which was utilized in a Suzuki coupling according to General Procedure A. The crude material was purified by reversed phase HPLC to give 350 (10 mg). MS (Q1) 452 (M)+

Aufarbeitung

  1. custombefore being quenched with water
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d0c41762a79f4076903201e811f9894b
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450315B2

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