Methyl 4-imidazolecarboxylate → methyl 1-(4-((2-amino-4-(mesitylenesulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)-1H-imidazole-5-carboxylate

HRID 2207102Notes

Reaction equation

HRID 2207102 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([O:13][C:14]1[C:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][C:22]=2[O:29][CH3:30])=[C:18]([CH3:31])[N:17]=[C:16]([NH2:32])[N:15]=1)(=[O:12])=[O:11].[NH:33]1[C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][N:35]=[CH:34]1>>[NH2:32][C:16]1[N:15]=[C:14]([O:13][S:10]([C:3]2[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=2[CH3:9])(=[O:12])=[O:11])[C:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:33]3[C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][N:35]=[CH:34]3)=[CH:23][C:22]=2[O:29][CH3:30])=[C:18]([CH3:31])[N:17]=1

Participants

3

Reactant 2

HCID 565661Methyl 4-imidazolecarboxylateHCID 879450752-Amino-5-(4-(chloromethyl)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 117992731methyl 1-(4-((2-amino-4-(mesitylenesulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)-1H-imidazole-5-carboxylateYield 15.1%

Procedure

The sub-title compound was synthesized by the method of example 1 step (vii) from the product of example 1 step (v) (500 mg) and Methyl 1H-imidazole-5-carboxylate (199 mg). The sub-title compound (90 mg) was obtained as a white solid; 1H NMR (300 MHz, CDCl3); 7.73 (1H, s), 7.61 (1H, s), 6.89 (2H, s), 6.83 (1H, d), 6.61 (1H, s), 6.55 (1H, d), 5.42 (2H, s), 3.78 (3H, s), 3.68 (5H, s), 2.46 (3H, s), 2.42 (6H, s), 2.26 (3H, s); LC-MS: m/z 566.

Sources & evidence

ORD record
ord-97fae1cd18b54d9392f524799da6095c
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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