2,4-Dichloropyrimidine → 2-Chloro-4-(4-phenylbut-1-ynyl)pyrimidine

HRID 334584Notes

Reaction equation

HRID 334584 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH2:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][C:11]#[CH:12]>>[Cl:1][C:2]1[N:7]=[C:6]([C:12]#[C:11][CH2:10][CH2:9][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 1233604-Phenyl-1-butyne

Product 1

HCID 117014952-Chloro-4-(4-phenylbut-1-ynyl)pyrimidineYield 69%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2,4-dichloropyrimidine (250 mg, 1.68 mmol) and 1-(but-3-ynyl)benzene (218 mg, 1.68 mmol). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1) to yield 280 mg (1.15 mmol, 69%) of 2-chloro-4-(4-phenylbut-1-ynyl)pyrimidine as a brown oil.

Workup

  1. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1)

Sources & evidence

ORD record
ord-a04d90c5fcfc4502b7bf1d9dc805c5f5
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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