Triethylamine → HCID 88954501, compound

HRID 1481252Notes

Reaction equation

HRID 1481252 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Cl:9][C:10]1[N:15]=[C:14](Cl)[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][N:11]=1.C(N(CC)CC)C>C1COCC1>[Cl:9][C:10]1[N:15]=[C:14]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 88954501HCID 88954501, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under external cooling with ice, 2.22 g (20.0 mmol) 4-fluoroaniline is added dropwise to a solution of 4.46 g (23.0 mmol) 2,4-dichloro-5-nitropyrimidine in 20 ml THF. Then a solution of 2.77 ml (20.0 mmol) triethylamine in 5 ml THF is added slowly under external cooling with ice. The reaction mixture is stirred for 1 hour at room temperature. The precipitate is filtered off and washed with THF. The filtrate is evaporated and crystallized from tert-butyl-methylether giving (2-chloro-5-nitro-pyrimidin-4-yl)-(4-fluoro-phenyl)-amine as yellow crystals; HPLC/MS (B): 2.26 min, [M+H] 269;

Workup

  1. temperatureunder external cooling with ice
  2. filtrationThe precipitate is filtered off
  3. washwashed with THF
  4. customThe filtrate is evaporated
  5. customcrystallized from tert-butyl-methylether

Sources & evidence

ORD record
ord-2edb71e5304c42938c9a94b992b4c927
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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