Water → HCID 178418729, Verbindung

HRID 473994

Reaktionsgleichung

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.C(NC(C)C)(C)C.[NH2:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=1.O>CN(C=O)C>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([NH:18][C:19]2[NH:20][N:21]=[C:22]([CH3:24])[CH:23]=2)[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a stirred solution of 4,6-dichloro-2-(methylthio)pyrimidine (25 g, 0.128 mol) in DMF (100 ml) was added diisopropylamine (19.8 g, 0.154 mol) followed by 3-amino-5-methylpyrazole (13.7 g, 0.154 mol) portionwise over 10 minutes. The solution was heated to 50° C. for 16 hours, after which time all of the starting material had reacted (by LC/MS analysis). The mixture was cooled to ambient and poured into water (250 ml). The precipitate was filtered and the wet solid slurried in diethyl ether (300 ml). The solid was again filtered and re-slurried in methanol (100 ml). The filtered product was air dried on the sinter, then further dried under vacuum. This affords the title compound as an off-white solid (22.1 g, 66% yield). 1H NMR (d6-DMSO) δ 2.22 (3H, s, CH3), 3.31 (3H, s, CH3), 6.00-7.50 (2H, br, CH), 10.17 (1H, s, NH), 12.10 (1H, s, NH); MS ES+256.08, ES−254.25.

Aufarbeitung

customafter which time all of the starting material had reacted (by LC/MS analysis)
temperatureThe mixture was cooled to ambient and
filtrationThe precipitate was filtered
filtrationThe solid was again filtered and re-slurried in methanol (100 ml)
customdried on the sinter
customfurther dried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-d250ddb18857464dbbd7e042437ef21b
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08637511B2

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