Dimethylformamide → HCID 57001654, compound

HRID 1264307Notes

Reaction equation

HRID 1264307 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2CN[C:15](=O)[NH:14][CH2:13]2)=[CH:8][CH:7]=1.CI.[CH3:22][N:23]([CH:25]=[O:26])[CH3:24]>C1COCC1>[CH3:3][O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:13][N:14]([CH3:15])[C:25](=[O:26])[N:23]([CH3:24])[CH2:22]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54013698HCID 54013698, compound

Product 1

HCID 57001654HCID 57001654, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) suspension of sodium hydride dispersion (60% in mineral oil (88 mg, 2.2 mmol) in THF (3 mL) is added a solution comprising of 4-(2-oxo-hexahydro-pyrimidin-5-yl)-benzoic acid methyl ester (236 mg, 1 mmol, reference example 95) and methyl iodide (300 μL, 5 mmol) in DMF (4 mL). The resulting mixture is stirred for 16 h. then quenched with water, diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated to give the title compound (255 mg) as a tan solid. 1H NMR (CDCl3) δ 2.98 (s, 6H), 3.37-3.53 (m, 5H), 3.93 (s, 3H), 7.32 (d, J=8 Hz, 2H), 8.01 (d, J=8 Hz, 2H). MS (ion spray) m/z 263 (M+H)+.

Workup

  1. temperatureTo a cooled
  2. customthen quenched with water
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f1969eeafcdc4250ac861c4078d643ab
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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