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

HRID 2381944Notes

Reaction equation

HRID 2381944 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:17][N:18]1[CH2:23][C:22]([CH3:24])=[N:21][NH:20][C:19]1=[O:25].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C>[CH3:24][C:22]1[CH2:23][N:18]([NH:17][C:14]([C:11]2[CH:12]=[N:13][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][CH:10]=2)=[O:16])[C:19](=[O:25])[NH:20][N:21]=1

Participants

5

Reactant 3

HCID 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 450733632-(3-Fluorophenyl)pyrimidine-5-carboxylic acid

Product 1

HCID 250996622-(3-Fluoro-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 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (0.317 g, 1.45 mmol) in anhydrous DMF (5 mL) is added 4-amino-6-methyl-4,5-dihydro-2H-[1,2,4]triazin-3-one (0.206 g, 1.45 mmol) followed by the addition of DMTMM (0.421 g, 1.52 mmol). The mixture is stirred at rt overnight. The mixture is partitioned between a saturated aqueous NaHCO3 solution and EtOAc. The organic phase is separated, dried (MgSO4), filtered and concentrated in vacuo to afford 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazin-4-yl)-amide (0.306 g) as a solid. MS: 329 (M+H).

Workup

  1. customThe mixture is partitioned between a saturated aqueous NaHCO3 solution and EtOAc
  2. customThe organic phase is separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d143cf9bac76409785882a6525b60655
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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