2,4-Dichlorobenzylamine → HCID 18449305, compound

HRID 1270204Notes

Reaction equation

HRID 1270204 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[Cl:11][C:12]1[N:13]=[C:14](Cl)[C:15]2[CH:21]=[CH:20][CH:19]=[N:18][C:16]=2[N:17]=1.C(N(CC)C(C)C)(C)C>ClCCCl.O>[Cl:11][C:12]1[N:13]=[C:14]([NH:5][CH2:4][C:3]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=2[Cl:1])[C:15]2[CH:21]=[CH:20][CH:19]=[N:18][C:16]=2[N:17]=1

Participants

6

Reactant 3

HCID 14852,4-DichlorobenzylamineHCID 81531DiisopropylethylamineHCID 222222282,4-Dichloro-pyrido[2,3-d]pyrimidine

Product 1

HCID 18449305HCID 18449305, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

2,4-Dichlorobenzylamine (211 mg, 1.2 mmol) was added to the stirred solution of 2,4 dichloro-pyrido[2,3-d]pyrimidine(200 mg, 1 mmol) and N,N-diisopropylethylamine (266 μL, 1.5 mmol) in 1,2-dichloroethane (5 mL). The reaction mixture was stirred at room temperature for 12 h and then diluted with water (10 mL). The aqueous layer was extracted with CH2Cl2 and the combined organic layer was washed with water (2×10 mL), dried (Na2SO4) and concentrated in vaccuo to give (2-Chloro-pyrido[2,3-d]pyrimidin-4-yl)-(2,4-dichloro-benzyl)-amine as a yellow oil (185 mg) and was used as such in the next reaction without further purification.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2
  2. washthe combined organic layer was washed with water (2×10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-baab083422ec49d09266dc149bd612eb
Source dataset
uspto-grants-2007_04
Patent number
US07202249B2

Reaction notes

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