2-Methoxyethanol → 2-{4-[4-(Acetyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-fluoropyrimidine

HRID 1441320Notes

Reaction equation

HRID 1441320 reaction equation
CN(C)/C=C(\[F:16])/C(C1N(C(C)C)C(C)=NC=1)=O.S([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:50]=[CH:49][C:31]([NH:32][C:33]3[N:38]=[C:37]([C:39]4[N:43]([CH:44]([CH3:46])[CH3:45])[C:42]([CH3:47])=[N:41][CH:40]=4)[C:36](Cl)=[CH:35][N:34]=3)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)(C)(=O)=O.C[O:52][CH2:53][CH2:54]O>>[C:53]([N:22]1[CH2:23][CH2:24][N:25]([C:28]2[CH:50]=[CH:49][C:31]([NH:32][C:33]3[N:38]=[C:37]([C:39]4[N:43]([CH:44]([CH3:46])[CH3:45])[C:42]([CH3:47])=[N:41][CH:40]=4)[C:36]([F:16])=[CH:35][N:34]=3)=[CH:30][CH:29]=2)[CH2:26][CH2:27]1)(=[O:52])[CH3:54]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 58127046(2Z)-3-(dimethylamino)-2-fluoro-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-oneHCID 686887152-[4-(4-Mesylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-chloropyrimidine

Product 1

HCID 114192152-{4-[4-(Acetyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-fluoropyrimidine

Procedure

A solution of (2Z)-3-(dimethylamino)-2-fluoro-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one (Method 14; 6.0 g, 25 mmol) and N-[4-(4-acetylpiperazin-1-yl)phenyl]guanidine bicarbonate salt (Method 2; 12.12 g, 37.5 mmol) in 2-methoxyethanol (90 ml) was heated under reflux for 18 hrs. The reaction mixture was evaporated under reduced pressure and the title compound was isolated by MPLC on silica gel (3% MeOH/DCM). It was obtained as a crisp foam on evaporation. Yield=8.9 g (81%). NMR: 1.36 (d, 6H), 2.03 (s, 3H), [2.5 (s, 3H) under DMSO signal], 2.98 (m, 2H), 3.08 (m, 2H), 3.57 (m, 4H), 5.44 (septuplet, 1H), 6.90 (d, 2H), 7.34 (d, 1H), 7.42 (d, 2H), 8.44 (d, 1H), 9.24 (s, 1H); m/z 438.

Workup

  1. temperatureunder reflux for 18 hrs
  2. customThe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f147664270b24cdd8134f2f61b823d89
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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