Water → HCID 178508022, compound

HRID 1525329Notes

Reaction equation

HRID 1525329 reaction equation
[N+:1]([C:4]1[C:5]([OH:16])=[N:6][C:7]([C:10]2[N:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:8][CH:9]=1)([O-])=O.O>C1COCC1.O>[NH2:1][C:4]1[C:5]([OH:16])=[N:6][C:7]([C:10]2[N:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 962WaterHCID 178526802HCID 178526802, compound2×

Product 1

HCID 178508022HCID 178508022, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 5-nitro-2-(pyridazin-3-yl)pyrimidin-4-ol, 35i-g, (3.0 g, 13.6 mmol) in THF/H2O (100 mL, VTHF/H2O=1:1) was added Na2S204 (4.77 g, 27.4 mmol) and stirred at room temperature for 4 h. The reaction mixture was extracted with EA (100 mL), washed with brine (50 mL), and concentrated under vacuum. The residue was purified by column chromatography to afford the product, 35i-h, (0.8 g, 30%) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ5.66 (s, 2H), 7.39 (s, 1H), 7.80 (dd, J=4.8, 8.4 Hz, 1H), 8.29 (d, J=8.4 Hz, 1H), 9.26 (d, J=4.8 Hz), LC-MS (M+H)+ 190.1.

Workup

  1. extractionThe reaction mixture was extracted with EA (100 mL)
  2. washwashed with brine (50 mL)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8530ff0729784f5bb681bd4c315504f8
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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