Sodium methanethiolate → HCID 136029932, compound

HRID 2382025Notes

Reaction equation

HRID 2382025 reaction equation
[CH3:1][C:2]1[CH2:3][N:4]([NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=3)=[N:16][CH:17]=2)=[O:11])[C:5](=[O:8])[NH:6][N:7]=1.C[S-].[Na+]>CN(C=O)C>[CH3:1][C:2]1[CH2:3][N:4]([NH:9][C:10]([C:12]2[CH:17]=[N:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[N:14][CH:13]=2)=[O:11])[C:5](=[O:8])[NH:6][N:7]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 59199960HCID 59199960, compound

Product 1

HCID 136029932HCID 136029932, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(4-methoxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazin-4-yl)-amide (100 mg, 0.29 mmol), sodium methanethiolate (206 mg, 2.9 mmol) and DMF (2 mL) is stirred at 110° C. for 6 h., and then cooled to rt. The reaction mixture is concentrated in vacuo, and the residue is purified on a reverse phase HPLC chromatography to afford 2-(4-hydroxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazin-4-yl)-amide (32 mg). MS: 327 (M+H); 1H NMR (DMSO-d6): δ 1.87 (s, 3H), 4.17 (s, 2H), 6.74 (m, 2H), 8.21 (d, J=6.9 Hz, 2H), 9.08 (s, 2H), 9.53 (s, 1H).

Workup

  1. temperaturecooled to rt
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customthe residue is purified on a reverse phase HPLC chromatography

Sources & evidence

ORD record
ord-56b63482917345b4a153e23413b9e50f
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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