4-Chloropyrimidine → 2-(4-(Pyrimidin-4-yl)but-3-ynyl)benzo[d]oxazole

HRID 1189128Notes

Reaction equation

HRID 1189128 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[CH2:8]([C:12]1[O:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1)[CH2:9][C:10]#[CH:11]>>[N:5]1[CH:6]=[CH:7][C:2]([C:11]#[C:10][CH2:9][CH2:8][C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 6428344-ChloropyrimidineHCID 860869072-(But-3-ynyl)benzo[d]oxazole

Product 1

HCID 665981222-(4-(Pyrimidin-4-yl)but-3-ynyl)benzo[d]oxazoleYield 17.3%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 4-chloropyrimidine (85 mg, 0.74 mmol) and 2-(but-3-ynyl)benzo[d]oxazole (127 mg, 0.74 mmol). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 3:2) to yield 32 mg (128 μmol, 17%) of 2-(4-(pyrimidin-4-yl)but-3-ynyl)benzo[d]oxazole as a white solid.

Workup

  1. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 3:2)

Sources & evidence

ORD record
ord-6cf8c76151d1442688bffa425affc14d
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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