Dimethylformamide → 1-Ethyl-3-(4-(4-morpholino-7-(pyrimidine-2-carbonyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1698008

Reaktionsgleichung

Reaktionsgleichung von HRID 1698008
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]([O-:9])=O.[Na+].CN(C)C=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.[CH2:47]([NH:49][C:50]([NH:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2[N:60]=[C:61]([N:69]3[CH2:74][CH2:73][O:72][CH2:71][CH2:70]3)[C:62]3[CH2:68][CH2:67][NH:66][CH2:65][C:63]=3[N:64]=2)=[CH:55][CH:54]=1)=[O:51])[CH3:48]>>[CH2:47]([NH:49][C:50]([NH:52][C:53]1[CH:54]=[CH:55][C:56]([C:59]2[N:60]=[C:61]([N:69]3[CH2:70][CH2:71][O:72][CH2:73][CH2:74]3)[C:62]3[CH2:68][CH2:67][N:66]([C:7]([C:2]4[N:1]=[CH:6][CH:5]=[CH:4][N:3]=4)=[O:9])[CH2:65][C:63]=3[N:64]=2)=[CH:57][CH:58]=1)=[O:51])[CH3:48]

Komponenten

7

Edukt 6

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23677639Sodium pyrimidine-2-carboxylateHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Produkt 1

HCID 592395521-Ethyl-3-(4-(4-morpholino-7-(pyrimidine-2-carbonyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Sodium pyrimidine-2-carboxylate (0.0229 g, 0.000157 mol) in dry N,N-Dimethylformamide (0.910 mL, 0.0118 mol) was added 1-Hydroxybenzotriazole (0.0313 g, 0.000232 mol) followed by N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.0409 g, 0.000213 mol) then followed by N,N-Diisopropylethylamine (0.0570 mL, 0.000327 mol) and then 1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0493 g, 0.000129 mol). The reaction mixture was stirred overnight. The reaction mixture was heated at 40° C. and stirred for 4 days. The reaction mixture was concentrated, chromatographed through silica gel (4 g, 0-10% MeOH in dichloromethane), and purified by HPLC. 1H NMR (500 MHz, DMSO) δ 8.99-8.94 (m, 1H), 8.68 (d, J=17.8, 1H), 8.24-8.06 (m, 2H), 7.66 (td, J=5.0, 2.2, 1H), 7.54-7.39 (m, 2H), 6.22-6.11 (m, 1H), 4.77 (s, 1H), 4.38 (s, 1H), 3.89 (d, J=5.2, 1H), 3.72 (dd, J=10.3, 5.7, 4H), 3.49 (dd, J=19.3, 4.3, 4H), 3.40 (d, J=5.3, 1H), 3.20-3.03 (m, 2H), 2.80 (s, 1H), 2.69 (s, 1H), 1.13-0.98 (m, 3H). LC/MS-m/z+489.2 (M+H)+.

Aufarbeitung

  1. stirringstirred for 4 days
  2. concentrationThe reaction mixture was concentrated
  3. customchromatographed through silica gel (4 g, 0-10% MeOH in dichloromethane)
  4. custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8a149a9eeefc40479c05c8a97c04c51f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163763B2

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