Hydrogen Peroxide → HCID 86304114, compound

HRID 2271477Notes

Reaction equation

HRID 2271477 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2N=[C:12]([CH2:14][C:15]3[CH:16]=[N:17][C:18]([C:21]#N)=[N:19][CH:20]=3)[CH:11]=[N:10][C:9]=2[O:23][CH3:24])[CH:5]=[CH:6][CH:7]=1.[OH-:25].[Na+].OO.[OH2:29].[CH3:30]O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:30]=[C:12]([CH2:14][C:15]3[CH:20]=[N:19][C:18]([C:21]([OH:29])=[O:25])=[N:17][CH:16]=3)[CH:11]=[N:10][C:9]=2[O:23][CH3:24])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 86304113HCID 86304113, compound

Product 1

HCID 86304114HCID 86304114, compoundYield 74%

Conditions

Temperature
50 °C

Procedure

A solution of 5-{[6-(3-chlorophenyl)-5-methoxypyrazin-2-yl]methyl}pyrimidine-2-carbonitrile (Example 22, 30 mg, 0.0845 mmol) in MeOH (1.54 mL) was heated to 50° C. until the starting material dissolved. 1 N aq. NaOH (0.23 mL, 0.23 mmol) was added followed by hydrogen peroxide (0.23 mL, 1.00 mol/L, 0.23 mmol) and the solution was heated at 50° C. for an additional 2 h. Water (5 mL) was added and the reaction was filtered and washed with water (3×5 mL). A mixture of products were observed; 5-{[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl}pyrimidine-2-carboxylic acid (the title compound) and 5-{[5-(3-chlorophenyl)-6-methoxypyridin-3-yl]methyl}pyrimidine-2-carboxamide (Example 24, 4 mg, 13%). The filtrated contained the acid, and the water layer was acidified with concentrated HCl (3 drops) and extracted with DCM (3×20 mL). The organic layers were combined, dried (Na2SO4), and concentrated under reduced pressure to afford the title compound (23 mg, 74%). 1H NMR (400 MHz, CD3OD) δ 8.86 (br s, 2H), 8.11 (d, J=1.96 Hz, 1H), 7.66 (d, J=1.96 Hz, 1H), 7.55 (s, 1H), 7.49-7.27 (m, 3H), 4.14 (br s, 2H), 3.94 (s, 3H). [M+H]=356.13

Workup

  1. dissolutiondissolved
  2. filtrationthe reaction was filtered
  3. washwashed with water (3×5 mL)
  4. additionA mixture of products
  5. extractionextracted with DCM (3×20 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ccc4352dcabf470d8cc585fab70b2006
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

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