4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → 4-(3-Chloro-4-fluoro-phenylamino)-5-{1-[5-(morpholine-4-carbonyl)-thiophen-2-yl]-methylidene}-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one

HRID 1072198

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

The mixture of 4-(3-chloro-4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (90 mg, 0.32 mmol), 5-(morpholine-4-carbonyl)-thiophene-2-carbaldehyde (82 mg, 0.36 mmol), and triethylamine (2 drops) in ethanol (3 mL) was heated at 90° C. oil bath for 2 hours, and cooled to room temperature. The solvent was evaporated and the residue was purified on a silica gel column eluting with methylene chloride-methanol (98:2 and 95:5) to provide pure 4-(3-chloro-4-fluoro-phenylamino)-5-{1-[5-(morpholine-4-carbonyl)-thiophen-2-yl]-methylidene}-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (41 mg, 28%). MS 486 [M++1].

Aufarbeitung

temperaturecooled to room temperature
customThe solvent was evaporated
customthe residue was purified on a silica gel column
washeluting with methylene chloride-methanol (98:2 and 95:5)

Quellen und Nachweise

ORD-Eintrag: ord-848b1f3373aa4a8c98d4b72e096f90db
Quelldatensatz: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06908930B2

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