2-Phenylpyrimidine-5-carboxylic acid → HCID 59199944, compound

HRID 2381970Notes

Reaction equation

HRID 2381970 reaction equation
[NH2:1][N:2]1[CH2:7][C:6]([CH3:8])=[N:5][N:4]([CH3:9])[C:3]1=[O:10].[C:11]1([C:17]2[N:22]=[CH:21][C:20]([C:23](O)=[O:24])=[CH:19][N:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C.CCOC(C)=O>[CH3:9][N:4]1[C:3](=[O:10])[N:2]([NH:1][C:23]([C:20]2[CH:19]=[N:18][C:17]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[N:22][CH:21]=2)=[O:24])[CH2:7][C:6]([CH3:8])=[N:5]1

Participants

6

Reactant 3

HCID 7473892-Phenylpyrimidine-5-carboxylic acidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 68552167HCID 68552167, compound

Product 1

HCID 59199944HCID 59199944, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-amino-2,6-dimethyl-4,5-dihydro-2H-1,2,4-triazin-3-one (0.219 g, 1.58 mmol) and 2-phenyl-pyrimidine-5-carboxylic acid (0.317 g, 1.58 mmol) in dry DMF (10 mL) under N2 is added DMTMM (0.46 g, 1.66 mmol). The mixture is stirred at rt for 22 h, then diluted with EtOAc (70 mL), and washed successively with saturated aqueous NaHCO3 solution (2×10 mL) and brine (10 mL). The organic phase is dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with heptane:EtOAc gradient to afford 2-phenyl-pyrimidine-5-carboxylic acid (2,6-dimethyl-3-oxo-2,5-dihydro-3H-1,2,4-triazin-4-yl)-amide as a solid (0.28 g, 55%). MS: 325 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 9.24 (s, 2H), 8.45 (dd, J=7.7, 2.0 Hz, 2 H), 7.52-7.62 (m, 3H), 4.25 (s, 2H), 3.18 (s, 3H), 1.95 (s, 3H).

Workup

  1. washwashed successively with saturated aqueous NaHCO3 solution (2×10 mL) and brine (10 mL)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel chromatography
  6. washeluting with heptane

Sources & evidence

ORD record
ord-85d65afdf0a14ab7b715aa3e5cc51143
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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