Nitrogen → 2-chloro-5-fluoro-N-(3-nitrophenyl)pyrimidin-4-amine

HRID 1482663Notes

Reaction equation

HRID 1482663 reaction equation
N#N.[Cl:3][C:4]1[N:9]=[C:8](Cl)[C:7]([F:11])=[CH:6][N:5]=1.[N+:12]([C:15]1[CH:21]=[CH:20][C:18](N)=[CH:17][CH:16]=1)([O-:14])=[O:13].CC[N:24](C(C)C)C(C)C>C(O)CCC.CCCCCC.C(OCC)(=O)C>[Cl:3][C:4]1[N:9]=[C:8]([NH:24][C:17]2[CH:18]=[CH:20][CH:21]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:7]([F:11])=[CH:6][N:5]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 74754-NitroanilineHCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 591746392-chloro-5-fluoro-N-(3-nitrophenyl)pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
120 °C

Procedure

In a 50 mL 3-neck RBF equipped with N2 bubbler and reflux condenser 2,4-dichloro-5-fluoropyrimidine (1.79 g) in 1-butanol (20 mL), 4-nitroaniline (1.0 g) and DIPEA (2.6 mL) were charge at room temperature. The reaction mixture was heated to 120° C. for 2 hr. The reaction was monitored on TLC using hexane:ethyl acetate (8:2) as mobile phase. After completion, the reaction mixture was cooled to room temperature. Solid precipitate was filtrated and washed with cold hexanes and dried to give 1.26 g of 2-chloro-5-fluoro-N-(3-nitrophenyl)pyrimidin-4-amine.

Workup

  1. additionwere charge at room temperature
  2. temperatureAfter completion, the reaction mixture was cooled to room temperature
  3. filtrationSolid precipitate was filtrated
  4. washwashed with cold hexanes
  5. customdried

Sources & evidence

ORD record
ord-7fb6b6a44c5146549f0dbf2c8ee90051
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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