Hydrogen Peroxide → 5-({6-[3-(Difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl}methyl)pyrimidine-2-carboxamide

HRID 2271473Notes

Reaction equation

HRID 2271473 reaction equation
[F:1][CH:2]([F:28])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[N:15]=[C:14]([CH2:16][C:17]3[CH:18]=[N:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=3)[CH:13]=[N:12][C:11]=2[O:25][CH2:26][CH3:27])[CH:7]=[CH:8][CH:9]=1.[OH-:29].[Na+].OO>CO>[F:28][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[N:15]=[C:14]([CH2:16][C:17]3[CH:18]=[N:19][C:20]([C:23]([NH2:24])=[O:29])=[N:21][CH:22]=3)[CH:13]=[N:12][C:11]=2[O:25][CH2:26][CH3:27])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 816897195-({6-[3-(Difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl}methyl)pyrimidine-2-carbonitrile

Product 1

HCID 863039555-({6-[3-(Difluoromethoxy)phenyl]-5-ethoxypyrazin-2-yl}methyl)pyrimidine-2-carboxamideYield 67.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-((6-(3-(difluoromethoxy)phenyl)-5-ethoxypyrazin-2-yl)methyl)pyrimidine-2-carbonitrile (Example 1, 100.00 mg, 0.26 mmol) in MeOH (1.3 mL) was added aq. NaOH (0.78 mL, 0.78 mmol), followed by hydrogen peroxide (0.78 mL, 0.79 mmol) The reaction mixture was stirred at room temperature for 8 h. The reaction mixture was concentrated, and the precipitate filtered and washed with water to obtain the title compound as a white solid (70 mg, 67%). 1H NMR (400 MHz, DMSO-d6) δ 8.93 (s, 2H), 8.27 (s, 1H), 8.12 (br s, 1H), 7.91-7.84 (m, 1H), 7.81 (t, J=1.8 Hz, 1H), 7.72 (br s, 1H), 7.52 (s, 1H), 7.44-7.02 (m, 2H), 4.42 (q, J=7.0 Hz, 2H), 4.25 (s, 2H), 1.35 (t, J=7.0 Hz, 3H). [M+H]=402.26.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationthe precipitate filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-8d54966c09224d9e9eb5be87a4b3800d
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

Loading…