Dimethylformamide → 2-(3-methoxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazin-4-yl)-amide

HRID 2381966Notes

Reaction equation

HRID 2381966 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.[NH2:18][N:19]1[CH2:24][C:23]([CH3:25])=[N:22][NH:21][C:20]1=[O:26].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-].CN(C=O)C>O>[CH3:25][C:23]1[CH2:24][N:19]([NH:18][C:15]([C:12]2[CH:13]=[N:14][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:10][CH:11]=2)=[O:17])[C:20](=[O:26])[NH:21][N:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 109755004-Amino-6-methyl-2,5-dihydro-1,2,4-triazin-3-oneHCID 532117402-(3-Methoxyphenyl)pyrimidine-5-carboxylic acid

Product 1

HCID 591999812-(3-methoxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazin-4-yl)-amideYield 64.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(3-methoxy-phenyl)-pyrimidine-5-carboxylic acid (135 mg, 0.58 mmol), 4-amino-6-methyl-4,5-dihydro-2H-[1,2,4]triazin-3-one (76 mg, 0.58 mmol), DMTMM (171 mg, 0.6 mmol) and DMF (3 mL) is stirred at rt for 2 days. Water (3 ml) is added, and the precipitated product is filtered, washed with water and dried to afford 2-(3-methoxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazin-4-yl)-amide (127 mg). MS: 341 (M+H); 1H NMR (DMSO-d6): δ 1.91 (s, 3H), 4.23 (s, 3H), 4.62 (s, 2H), 7.53 (m, 2H), 8.34 (m, 1H), 8.46 (s, 1H), 9.27 (s, 2H), 9.97 (s, 1H), 11.08 (s, 1H). IC50=174.5 nM.

Workup

  1. filtrationthe precipitated product is filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-15b205fa61e24841bfbd561fea4ff5fd
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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