Sodium Methoxide → 2-{4-[4-(2-Methoxyethylsulphonyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

HRID 1441315Notes

Reaction equation

HRID 1441315 reaction equation
[CH3:1][O-:2].[Na+].[CH:4]([S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:36]=[CH:35][C:18]([NH:19][C:20]3[N:25]=[C:24]([C:26]4[N:30]([CH:31]([CH3:33])[CH3:32])[C:29]([CH3:34])=[N:28][CH:27]=4)[CH:23]=[CH:22][N:21]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])=[O:7])=[CH2:5]>CO>[CH3:1][O:2][CH2:5][CH2:4][S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:36]=[CH:35][C:18]([NH:19][C:20]3[N:25]=[C:24]([C:26]4[N:30]([CH:31]([CH3:32])[CH3:33])[C:29]([CH3:34])=[N:28][CH:27]=4)[CH:23]=[CH:22][N:21]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)(=[O:7])=[O:8]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 686838262-{4-[4-(Vinylsulphonyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

Product 1

HCID 445786162-{4-[4-(2-Methoxyethylsulphonyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (40 mg 0.74 mmol) was added to 2-{4-[4-(vinylsulphonyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine (Example 29; 300 mg 0.64 mmol) in MeOH (4 ml). After stirring at room temperature for 5 hours, the reaction was evaporated. After chromatography on silica gel using MeOH:DCM:EtOAc (5:47.5:47.5) and trituration with ether, the title compound was obtained as a yellow solid. NMR: 1.41 (d, 6H), 2.47 (s, 3H), 3.13 (m, 4H), 3.26 (4H alongside exchangeables), 3.37 (t, 2H), 3.67 (t, 2H), 5.69 (septuplet, 1H), 6.93 (d, 2H), 6.96 (d, 1H), 7.39 (s, 1H), 7.49 (d, 2H), 8.32 (d, 1H), 9.18 (s, 1H); m/z 500.

Workup

  1. customthe reaction was evaporated

Sources & evidence

ORD record
ord-6e377fe5420446aa9da4e6eaf7b4e7b7
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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