Sodium hydride → HCID 58739081, compound

HRID 720289Notes

Reaction equation

HRID 720289 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](S(C)(=O)=O)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2].[CH3:26][C:27]1[N:31]=[CH:30][NH:29][N:28]=1.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:29]2[CH:30]=[N:31][C:27]([CH3:26])=[N:28]2)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21060065HCID 21060065, compoundHCID 178433329HCID 178433329, compound

Product 1

HCID 58739081HCID 58739081, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
24 °C

Procedure

A solution of 5-benzyloxy-2-methanesulfonyl-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (1.00 g, 2.73 mmol) and 3-methyl-1H-[1,2,4]triazole (0.272 g, 3.27 mmol) in dry N,N-dimethylformamide (10 ml) at 0° C. was treated with sodium hydride (0.16 g of a 60% dispersion in mineral oil, 4.0 mmol) and the resulting mixture was stirred at 0° C. for 30 min and at 24° C. for another 30 min. The reaction mixture was then quenched with acetic acid (0.2 ml) and the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and chromatography on silica gel (elution toluene-acetone 90:10 to 85:15) first gave 0.358 g (35% yield) of 5-benzyloxy-1-methyl-2-(3-methyl-[1,2,4]triazol-1-yl)-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.34 (3H, t, J=7.1 Hz, CH3), 2.51 (3H, s, CH3), 3.73 (3H, s, NCH3), 4.37 (2H, q, J=7.1 Hz, CH2), 5.37 (2H, s, OCH2), 7.40 (3H, m, aromatics), 7.50 (2H, m, aromatics), 8.71 (1H, s, CH). HRMS (FAB POS) calculated for C18H20N5O4 [M+H+]: 370.14. found: 370.14. The following fractions then gave 0.395 g (39% yield) of 5-benzyloxy-1-methyl-2-(5-methyl-[1,2,4]triazol-1-yl)-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.33 (3H, t, J=7.0 Hz, CH3), 2.67 (3H, s, CH3), 3.52 (3H, s, NCH3), 4.37 (2H, q, J=7.0 Hz, CH2), 5.41 (2H, s, OCH2), 7.40 (3H, m, aromatics), 7.51 (2H, m, aromatics), 8.00 (1H, s, CH). HRMS (FAB POS) calculated for C18H20N5O4 [M+H+]: 370.14. found: 370.14.

Workup

  1. customThe reaction mixture was then quenched with acetic acid (0.2 ml)
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-ced80ad8de7f429795336b807497710f
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

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