Triethylamine → N-{4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl}prop-2-enamide

HRID 1698964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698964
[NH2:1][C:2]1[N:19]=[CH:18][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=3)[C:4]=2[CH:3]=1.CCN(CC)CC.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29].CO.CCOC(C)=O>C1COCC1.CN(C1C=CN=CC=1)C>[Br:17][C:13]1[CH:12]=[C:11]([NH:10][C:9]2[C:4]3[CH:3]=[C:2]([NH:1][C:27](=[O:30])[CH:28]=[CH2:29])[N:19]=[CH:18][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 13140Acryloyl chloride2×HCID 53282584-N-(3-bromophenyl)pyrido[3,4-d]pyrimidine-4,6-diamineHCID 21584119Ethylacetate methanol2×

Produkt 1

HCID 5329069N-{4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl}prop-2-enamideAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6-amino-4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidine (J Med Chem, 1996;39:1823) (455 mg, 1.50 mmol) in dry THF (50 mL) at 0° C. under N2 was added Et3N (22.5 mmol, 1.61 mL), a catalytic amount of DMAP (45 mg) and acryloyl chloride (4.50 mmol, 366 μL). The reaction mixture was stirred for 1 hour and then additional acryloyl chloride (100 μL) was added and the reaction was allowed to warm to room temperature and stirred for another hour before being worked up as in the previous example, to give after column chromatography on silica gel eluting with MeOH/EtOAc (5:95), N-[4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl]acrylamide (20 mg, 37%) as a cream powder, mp (EtOAc/MeOH) 238-245° C. (dec.).

Aufarbeitung

  1. stirringstirred for another hour

Quellen und Nachweise

ORD-Eintrag
ord-d5dffe6bdf8f42e095bece0349ff040f
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344459B1

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