2,4-Dichloropyrimidine → 2-chloro-N-(2,4,6-trifluorobenzyl)pyrimidin-4-amine

HRID 929914Notes

Reaction equation

HRID 929914 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([F:11])[C:3]=1[CH2:4][NH2:5].[Cl:12][C:13]1[N:18]=[C:17](Cl)[CH:16]=[CH:15][N:14]=1.CCN(C(C)C)C(C)C>CC(O)C>[Cl:12][C:13]1[N:18]=[C:17]([NH:5][CH2:4][C:3]2[C:2]([F:1])=[CH:9][C:8]([F:10])=[CH:7][C:6]=2[F:11])[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 27770462,4,6-Trifluorobenzylamine

Product 1

HCID 1181551712-chloro-N-(2,4,6-trifluorobenzyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2,4,6-trifluorobenzylamine (5 g, 31 mmol) was added dropwise to a stirred suspension of 2,4-dichloropyrimidine (4.6 g, 31 mmol) and DIPEA (5.4 mL, 62 mmol) in IPA (100 mL) at 0° C. then the reaction mixture was warmed to room temperature and stirred overnight. The precipitate was collected and washed with diethyl ether to afford the first crop of 2-chloro-N-(2,4,6-trifluorobenzyl)pyrimidin-4-amine IV-1. The filtrate was concentrated and purified by column chromatography (0-30% v/v ethyl acetate/petrol) to afford a second crop (total yield 5.3 g, 62%). LC-MS (Method F), RT=2.27 min. (ES+) 274.

Workup

  1. customThe precipitate was collected
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-76dab07f299541c59727062031c6abfd
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

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