Hydrochloric Acid → 6-Chloro-N4-(4-trifluoromethyl-phenyl)-pyrimidine-4,5-diamine hydrochloride

HRID 60196

Reaction equation

HRID 60196 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].[F:10][C:11]([F:20])([F:19])[C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.Cl>CCO>[ClH:8].[Cl:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([C:11]([F:10])([F:19])[F:20])=[CH:13][CH:14]=2)[C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 99644-(Trifluoromethyl)anilineHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 866312666-Chloro-N4-(4-trifluoromethyl-phenyl)-pyrimidine-4,5-diamine hydrochlorideYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-amino-4,6-dichloropyrimidine (10.0 g, 61.0 mmol, 1.0 eq), 4-trifluoromethylaniline (8.34 mL, 67.1 mmol, 1.1 eq), EtOH (80 mL), and concentrated HCl (2.5 mL, 30.5 mmol, 0.5 eq) was heated to 80° C. for 24 h and then cooled to rt. The resulting precipitate was collected by filtration, rinsed with EtOH, and dried under vacuum at 50° C. for 18 h to provide the title compound as a white solid (13.9 g, 70%). MS (ESI): mass calcd. for C11H9ClF3N4 [M+H]+, 289.0; m/z found, 289.0. 1H NMR (d6-DMSO): 9.26 (s, 1H), 8.01 (d, J=8.5 Hz, 2H), 7.94 (s, 1H), 7.67 (d, J=8.6 Hz, 2H), 6.41 (br s, 3H).

Workup

  1. temperaturecooled to rt
  2. filtrationThe resulting precipitate was collected by filtration
  3. washrinsed with EtOH
  4. customdried under vacuum at 50° C. for 18 h

Sources & evidence

ORD record
ord-772409fb207d47ce82807bc0702d7595
Source dataset
uspto-grants-2016_09
Patent number
US09440978B2

Linked notes

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