Hydrochloric Acid → HCID 10134174, compound

HRID 2084126Notes

Reaction equation

HRID 2084126 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)[N:3]=1.[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:21]=1[NH2:22].Cl.[OH-].[Na+]>O.C(O)C>[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:21]=1[NH:22][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76132,5-DimethoxyanilineHCID 14798Sodium HydroxideHCID 227323674-Chloro-2-(2-pyrazinyl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 10134174HCID 10134174, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-chloro-2-(2-pyrazinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.192 mmol), 2,5-dimethoxyaniline and aqueous 2N HCl (150 μl) in water:ethanol (1:1, 10 ml) was refluxed for 48 h. The mixture was cooled to room temperature and then basified with aqueous 2N NaOH to pH 10-12. The resulting precipitate was filtered, washed with water, water:ethanol (2:1) and isolated as a green-yellow solid (46 mg, 64%). 1H NMR (CDCl3): 9.74 (d, J=1.5 Hz, 1H), 8.79 (dd, J=1.8, 2.4 Hz, 1H), 8.72 (d, J=2.4 Hz, 1H), 7.80 (bs, 1H), 7.70 (s, 1H), 7.07 (s, 1H), 6.91 (d, J=9.3 Hz, 1H), 6.72 (dd, J=3.0, 9.0 Hz, 1H), 3.87 (s, 3H), 3.86 (s, 3H).

Workup

  1. temperaturewas refluxed for 48 h
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water, water:ethanol (2:1)

Sources & evidence

ORD record
ord-7648ab7ded0a4ec8888c9911f9d607fd
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

Loading…