Allyl isocyanate → 6-Arylpyrido[2,3-d]pyrimidine deriv. 52

HRID 3427

Reaktionsgleichung

Reaktionsgleichung von HRID 3427
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:29]([NH2:30])=[N:28][C:12]2[N:13]=[C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[N:15]=[CH:16][C:11]=2[CH:10]=1.[CH2:31]([N:34]=[C:35]=[O:36])[CH:32]=[CH2:33]>>[CH2:31]([NH:34][C:35]([NH:30][C:29]1[C:9]([C:3]2[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:10][C:11]2[CH:16]=[N:15][C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)=[N:13][C:12]=2[N:28]=1)=[O:36])[CH:32]=[CH2:33]

Komponenten

3

Edukt 2

HCID 15123Allyl isocyanateHCID 53281486-(2,6-dichlorophenyl)-2-N-[3-(4-methylpiperazin-1-yl)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine

Produkt 1

HCID 53281546-Arylpyrido[2,3-d]pyrimidine deriv. 52Ausbeute 26,2 %

Versuchsvorschrift

6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 0.186 g of allyl isocyanate according to the general procedure of Example 37. The product was purified by chromatography and crystallized from ethyl acetate to give 0.31 g of 1-allyl-3-{6-(2,6-dichlorophenyl)-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-pyrido[2,3-d]pyrimidin-7-yl}-urea, ESMS (20/80 MeOH/CH3CN+0.1% AcOH): M+ +H=529 (Base), 472, 446; mp 104°-108° C.

Aufarbeitung

  1. customThe product was purified by chromatography
  2. customcrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8d255ebcb23144a4b195e3bc10791314
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733913

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