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

HRID 578831Notes

Reaction equation

HRID 578831 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-7a91cced1408437c8cd14cf83e544572
Source dataset
uspto-grants-2015_05
Patent number
US09040692B2

Reaction notes

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