Glyoxal → HCID 58174204, compound

HRID 1255911Notes

Reaction equation

HRID 1255911 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][O:18][C:19]3[N:24]=[CH:23][N:22]=[C:21]([NH2:25])[C:20]=3[NH2:26])=[CH:12][CH:11]=2)[CH:4]=1.[CH:29]([CH:31]=O)=O>CCO>[F:28][C:2]([F:1])([F:27])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][O:18][C:19]3[C:20]4[C:21](=[N:25][CH:29]=[CH:31][N:26]=4)[N:22]=[CH:23][N:24]=3)=[CH:14][CH:15]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 58174078HCID 58174078, compound

Product 1

HCID 58174204HCID 58174204, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

6-{2-[4-(4-Trifluoromethylpyridin-2-yloxy)-phenyl]-ethoxy}-pyrimidine-4,5-diamine (75 mg, 0.19 mmol) was combined with 50% aqueous glyoxal solution (1 mL) in EtOH (5 mL) and stirred overnight at 25° C. The solution was evaporated and the residue extracted with CH2Cl2. The CH2Cl2 layer was washed with H2O and concentrated in vacuo. The residue was recrystallized from hot MeCN to give 4-{2-[4-(4-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethoxy}-pteridine (16 mg, 20%): mp 172-173° C.; EIMS m/z 413; 1H NMR (300 MHz, CDCl3) δ 9.24 (s, 1H), 9.07 (s, 1H), 9.02 (s, 1H), 8.30 (s, 1H), 7.43 (d, J=9.5 Hz, 2H), 7.28 (d, J=9.0 Hz, 2H), 4.63 (t, 6.8 Hz, 2H), 3.17 (t, J=7.0 Hz, 2H).

Workup

  1. customThe solution was evaporated
  2. extractionthe residue extracted with CH2Cl2
  3. washThe CH2Cl2 layer was washed with H2O
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from hot MeCN

Sources & evidence

ORD record
ord-84a6b4696de04ae48cdb2453a491871f
Source dataset
uspto-grants-2013_06
Patent number
US08461164B2

Reaction notes

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