2,4-Dichloropyrimidine → 2-(4-(2-Chloropyrimidin-4-yl)but-3-ynyl)benzo[d]oxazole

HRID 1189111Notes

Reaction equation

HRID 1189111 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH2:9]([C:13]1[O:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=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[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 860869072-(But-3-ynyl)benzo[d]oxazole

Product 1

HCID 116377492-(4-(2-Chloropyrimidin-4-yl)but-3-ynyl)benzo[d]oxazoleYield 9%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2,4-dichloropyrimidine (200 mg, 1.34 mmol) and 2-(but-3-ynyl)benzo[d]oxazole (230 mg, 1.34 mmol, Example 8(A)) at room temperature. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1) to yield 35 mg (0.12 mmol, 9%) of 2-(4-(2-chloropyrimidin-4-yl)but-3-ynyl)benzo[d]oxazole as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-b21ee79171b64248978de6cebfafd6f9
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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