Dimethylformamide → 2-Methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carboxylic acid (2-methoxy-ethyl)-amide

HRID 2262116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2262116
Cl[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]([CH:11]=[O:12])=[CH:8][C:6]=2[N:7]=1.[C:19](Cl)(=O)C(Cl)=O.CN(C)C=O.[CH3:30][O:31][CH2:32][CH2:33][NH2:34]>ClCCl.C(N(CC)CC)C>[CH3:30][O:31][CH2:32][CH2:33][NH:34][C:11]([C:9]1[S:10][C:5]2[C:4]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:3][C:2]([CH3:19])=[N:7][C:6]=2[CH:8]=1)=[O:12]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 80182-MethoxyethylamineHCID 65578Oxalyl chlorideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Produkt 1

HCID 671902602-Methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carboxylic acid (2-methoxy-ethyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel3×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To 2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde 10 in dichloromethane (2 ml) was added 2M oxalyl chloride solution in dichloromethane (0.75 ml) followed by 2 microdrops of dimethylformamide. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo to give a crude product. This crude product was stirred in dichloromethane (5 ml) and to it was added 2-methoxyethylamine (34.8 μL) and triethylamine (61.5 μL). The reaction mixture was stirred at room temperature overnight. It was then partitioned between dichloromethane and saturated sodium bicarbonate solution, the combined organics were dried (MgSO4) and the solvents removed in vacuo to give a crude residue. This was purified by flash chromatography to yield 2-Methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carboxylic acid (2-methoxy-ethyl)-amide (30 mg).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customto give a crude product
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. customIt was then partitioned between dichloromethane and saturated sodium bicarbonate solution
  5. dry with materialthe combined organics were dried (MgSO4)
  6. customthe solvents removed in vacuo
  7. customto give a crude residue
  8. customThis was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e24490a36ed24d9a846df73699254e2c
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846929B2

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