Ammonium Acetate → HCID 86671416, compound

HRID 1618959Notes

Reaction equation

HRID 1618959 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([Cl:11])[N:6]=1)=O.[O:12]=[C:13]1[CH2:29][C:28](=O)[C:16]2([CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18][CH2:17]2)[CH2:15][NH:14]1.C([O-])(=O)C.[NH4+:35]>CCO>[Cl:11][C:7]1[N:6]=[C:5]([C:3]2[NH:35][C:28]3[C:16]4([CH2:17][CH2:18][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20]4)[CH2:15][NH:14][C:13](=[O:12])[C:29]=3[CH:2]=2)[CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 68315272HCID 68315272, compoundHCID 72942891HCID 72942891, compound

Product 1

HCID 86671416HCID 86671416, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(2-chloropyrimidin-4-yl)ethanone (1.04 mmol, 0.24 g), D6 (1.04 mmol, 0.28 g) and ammonium acetate (4.15 mmol, 0.32 g) in EtOH (20 mL) was stirred at room temperature for 1 hour. The reaction mixture was concentrated. The residue was taken up in water (20 mL) and brought to pH 7 with 5% aqueous NaHCO3. The precipitate was filtered off and purified by flash silicagel chromatography (100% DCM to 10% MeOH) yielding 0.11 g of a yellow solid (26%). 1H-NMR (400 MHz, CDClb, 300K): δ=1.49 (9H, s), 2.28 (2H, m), 3.55 (6H, m), 5.70 (1H, br s), 7.30 (1H, s), 7.39 (1H, d, J=5.3 Hz), 8.50 (1H, d, J=5.3 Hz), 9.84 (1H, br s); MS (ES) C19H22ClN5O3 requires: 403. found: 404.2 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe precipitate was filtered off
  3. custompurified by flash silicagel chromatography (100% DCM to 10% MeOH)

Sources & evidence

ORD record
ord-3a2f403a07584b5880bef08497b050f6
Source dataset
uspto-grants-2014_07
Patent number
US08772286B2

Reaction notes

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