Sodium → 4-[2-(4-Trifluoromethylphenyl)-pyrimidin-4-yl]-phenylamine

HRID 1475155Notes

Reaction equation

HRID 1475155 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.[Na].O.O.Cl.FC(F)(F)C1C=CC(C(N)=N)=CC=1>CCO.C(Cl)(Cl)Cl.CCOC(C)=O>[F:25][C:22]([F:23])([F:24])[C:19]1[CH:18]=[CH:17][C:16]([C:12]2[N:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH:15]=[CH:14][N:13]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 5360545SodiumHCID 446307714-(Trifluoromethyl)benzene-1-carboximidamide--hydrogen chloride--water (1/1/2)HCID 669685764-(4-Nitrophenyl)-2-(4-trifluoromethylphenyl)-pyrimidine

Product 1

HCID 669688834-[2-(4-Trifluoromethylphenyl)-pyrimidin-4-yl]-phenylamineYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 21584013Chloroform ethylacetateSolvent2×

Procedure

4-(4-Nitrophenyl)-2-(4-trifluoromethyl-phenyl)-pyrimidine. To 82.7 mg (3.60 mmol) of sodium metal dissolved in 3 mL of absolute EtOH was added 938 mg (3.60 mmol) of 4-trifluoromethylbenzamidine hydrochloride dihydrate followed by 4 mL of EtOH. After 30 min, 498 mg (2.26 mmol) of 3-dimethylamino-1-(4-nitrophenyl)-propenone was added and the mixture was heated at reflux approximately 66 h and was allowed to cool. The mixture was concentrated to a tan solid which was triturated under saturated sodium bicarbonate. The solid was collected and air dried to give 937 mg. It was then dissolved in chloroform/EtOAc and was passed over silica gel eluting with 7:3 chloroform/EtOAc to afford 710 mg (91%) of the title compound. 1H NMR δ 9.01 (d, J=5.3 Hz, 1H), 8.73 (d, J=8.2 Hz, 2H), 8.43 (s, 4H), 7.82 (d, J=8.1 Hz, 2H), 7.76 (d, J=5.2 Hz, 1H); EIMS 345 (M+, 100), 299 (57); mp 175-176.5° C. Anal. Calcd. for C17H10F3N3O2: C, 59.13; H, 2.92; N, 12.17. Found: C, 58.82; H, 2.63; N, 11.98.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux approximately 66 h
  3. temperatureto cool
  4. concentrationThe mixture was concentrated to a tan solid which
  5. customwas triturated under saturated sodium bicarbonate
  6. customThe solid was collected
  7. customair dried
  8. customto give 937 mg

Sources & evidence

ORD record
ord-b20d6db910dc4b02848441d8459148a6
Source dataset
uspto-grants-2015_04
Patent number
US09018363B2

Reaction notes

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