(E)-3-(Dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one → 2-[4-(4-Acetylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

HRID 1441306Notes

Reaction equation

HRID 1441306 reaction equation
CN(C)/C=[CH:4]/[C:5](C1N(C(C)C)C(C)=NC=1)=[O:6].S([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:49]=[CH:48][C:30]([NH:31][C:32]3[N:37]=[C:36]([C:38]4[N:42]([CH:43]([CH3:45])[CH3:44])[C:41]([CH3:46])=[N:40][CH:39]=4)[C:35](Cl)=[CH:34][N:33]=3)=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)(C)(=O)=O>COCCO>[C:5]([N:21]1[CH2:22][CH2:23][N:24]([C:27]2[CH:28]=[CH:29][C:30]([NH:31][C:32]3[N:37]=[C:36]([C:38]4[N:42]([CH:43]([CH3:45])[CH3:44])[C:41]([CH3:46])=[N:40][CH:39]=4)[CH:35]=[CH:34][N:33]=3)=[CH:48][CH:49]=2)[CH2:25][CH2:26]1)(=[O:6])[CH3:4]

Participants

4

Reactant 2

HCID 22273494(E)-3-(Dimethylamino)-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 113160942-[4-(4-Acetylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

(2E)-3-(Dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one (Method 24 of WO 03/076436; 140 mg 0.63 mmol) and N-[4-(4-acetylpiperazin-1-yl)phenyl]guanidine bicarbonate salt (Method 2; 240 mg 0.74 mmol) in 2-methoxyethanol (4 ml) were reacted under nitrogen under microwave conditions at 200° C. for 30 minutes. After evaporation under reduced pressure, chromatography on silica gel with MeOH:DCM (2:98 to 6:94) gave the title compound, after ether trituration, as a yellow solid. (85 mg 31.5%). NMR: 1.39 (d, 6H), 2.02 (s, 3H), 2.45 (s, 3H), 3.00 (b t, 2H), 3.06 (b t, 2H), 3.56 (b q, 4H), 5.70 (septuplet, 1H), 6.91 (d, 2H), 6.95 (d, 1H), 7.38 (s, 1H), 7.46 (d, 2H), 8.31 (d, 1H), 9.15 (s, 1H); m/z 420.

Workup

  1. customAfter evaporation under reduced pressure, chromatography on silica gel with MeOH:DCM (2:98 to 6:94)

Sources & evidence

ORD record
ord-80c37b4d681e4575aba095b30de752f2
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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