Potassium Carbonate → HCID 67502537, compound

HRID 1887200Notes

Reaction equation

HRID 1887200 reaction equation
[C:1]([O:5][C:6](=[O:22])[C@@H:7]([N:10]1[C:15](=[O:16])[C:14]2[N:17]=[CH:18][CH:19]=[CH:20][C:13]=2[NH:12][C:11]1=[O:21])[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].Br[CH2:24][C:25]1[C:29]2[C:30]([CH3:35])=[CH:31][C:32]([CH3:34])=[CH:33][C:28]=2[S:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([O:5][C:6](=[O:22])[C@@H:7]([N:10]1[C:15](=[O:16])[C:14]2[N:17]=[CH:18][CH:19]=[CH:20][C:13]=2[N:12]([CH2:24][C:25]2[C:29]3[C:30]([CH3:35])=[CH:31][C:32]([CH3:34])=[CH:33][C:28]=3[S:27][N:26]=2)[C:11]1=[O:21])[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 584973913-Bromomethyl-4,6-dimethyl-benzo[d]isothiazoleHCID 67503155HCID 67503155, compound

Product 1

HCID 67502537HCID 67502537, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 46 mg of (S)-2-(2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl)-butyric acid tert-butyl ester, 41 mg of 3-bromomethyl-4,6-dimethyl-1,2-benzoisothiazole and 111 mg of potassium carbonate is stirred at room temperature for 4 h. The reaction mixture is diluted with water and the product is filtered and washed with water. The isolated solid is purified by flash chromatography on silica gel to give 72 mg (99%) of (S)-2-[1-(4,6-dimethyl-benzo[d]isothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl]-butyric acid tert-butyl ester.

Workup

  1. filtrationthe product is filtered
  2. washwashed with water
  3. customThe isolated solid is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-29684024931340509b8319ffc0404d0d
Source dataset
uspto-grants-2013_08
Patent number
US08501749B2

Reaction notes

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