Diisopropylethylamine → (4-Methylpiperazin-1-yl)-[3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)phenyl]methanone

HRID 1805989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805989
[Cl:1][C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.CN(C(ON1N=[N:36][C:31]2C=[CH:33][CH:34]=[N:35][C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:45](N(C(C)C)CC)(C)C.ClC1N=C(CCCN)C2S(=O)(=O)CCC=2N=1>CS(C)=O>[CH3:45][N:35]1[CH2:30][CH2:31][N:36]([C:15]([C:14]2[CH:18]=[CH:19][CH:20]=[C:12]([NH:11][C:4]3[C:5]4[S:10][CH2:9][CH2:8][C:6]=4[N:7]=[C:2]([Cl:1])[N:3]=3)[CH:13]=2)=[O:17])[CH2:33][CH2:34]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 576001073-(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acidHCID 86616274(2-chloro-5,5-dioxo-6,7-dihydro-5H-5lambda6-thieno[3,2-d]pyrimidin-4-yl)propylamine

Produkt 1

HCID 86616277(4-Methylpiperazin-1-yl)-[3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)phenyl]methanoneAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

0.600 g (1.95 mmol) of 3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acid (I), 0.741 g (1.95 mmol) of O-(7-azabenzotriazol-1-yl-)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU), and 0.680 mL (3.90 mmol) of is diisopropylethylamine are placed in 10 mL of dimethylsulfoxide, then stirred for 0.5 hours at ambient temperature. 0.220 mL (1.95 mmol) of methylpiperazine (II) is added, then the mixture is stirred for 3 hours at ambient temperature. Then the reaction mixture is concentrated by evaporation and the residue is combined with water. Any precipitate formed is suction filtered and dried. The crude product is purified by chromatography through a 50 g silica cartridge with ethyl acetate/methanol 8:2. 0.250 g of product III (33%) is obtained.

Aufarbeitung

  1. stirringthe mixture is stirred for 3 hours at ambient temperature
  2. concentrationThen the reaction mixture is concentrated by evaporation
  3. customAny precipitate formed
  4. filtrationfiltered
  5. customdried
  6. customThe crude product is purified by chromatography through a 50 g silica cartridge with ethyl acetate/methanol 8:2

Quellen und Nachweise

ORD-Eintrag
ord-576ddd9f4f8845ffb8b3373a93bf99fd
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354531B2

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