Potassium Iodide → Ethyl 2-((4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(ethyl)amino)acetate

HRID 2207065Notes

Reaction equation

HRID 2207065 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].C(OC([O-])=O)([O-])=O.[K+].[K+].[I-].[K+].[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:23]=1[S:30]([O:33][C:34]1[C:39]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([CH2:47]Cl)=[CH:43][C:42]=2[O:49][CH3:50])=[C:38]([CH3:51])[N:37]=[C:36]([NH2:52])[N:35]=1)(=[O:32])=[O:31]>C(#N)C>[NH2:52][C:36]1[N:35]=[C:34]([O:33][S:30]([C:23]2[C:22]([CH3:21])=[CH:27][C:26]([CH3:28])=[CH:25][C:24]=2[CH3:29])(=[O:31])=[O:32])[C:39]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([CH2:47][N:3]([CH2:1][CH3:2])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:43][C:42]=2[O:49][CH3:50])=[C:38]([CH3:51])[N:37]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 12591597Ethyl 2-(ethylamino)acetateHCID 86587255Potassium dicarbonateHCID 879450752-Amino-5-(4-(chloromethyl)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 117992606Ethyl 2-((4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(ethyl)amino)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

The product from step (vi) (390 mg) was added to the mixture of potassium dicarbonate (410 mg), potassium iodide (49 mg) and the crude product from step (v) in acetonitrile (5 mL). After the mixture was stirred at 70° C. for 4 h, the reaction mixture was cooled to RT, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography to afford the sub-title compound (490 mg) as a colourless amorphous solid; 1H NMR (300 MHz, CDCl3); 6.91 (2H, s), 6.87 (1H, s), 6.72 (2H, s), 4.65 (2H, br s), 4.14 (2H, q), 3.82-3.79 (5H, m), 3.70 (2H, s), 3.28 (2H, s), 2.67 (2H, q), 2.56 (6H, s), 2.28 (3H, s), 2.23 (3H, s), 1.25 (3H, t), 1.07 (3H, t).

Workup

  1. temperaturethe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-d1a4c0816a844a138f9830cd1f043d88
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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