4-Butoxybenzaldehyde → 3-(Pyrimidin-5-yloxy)-4,5-dihydroisoxazole

HRID 1746127Notes

Reaction equation

HRID 1746127 reaction equation
C(OC1C=CC(C=O)=CC=1)CCC.Br[C:15]1[CH2:19][CH2:18][O:17][N:16]=1.[OH:20][C:21]1[CH:22]=[N:23][CH:24]=[N:25][CH:26]=1>>[N:23]1[CH:22]=[C:21]([O:20][C:15]2[CH2:19][CH2:18][O:17][N:16]=2)[CH:26]=[N:25][CH:24]=1

Participants

4

Reactant 3

HCID 798134-ButoxybenzaldehydeHCID 565855Pyrimidin-5-olHCID 219834983-Bromo-4,5-dihydroisoxazole

Product 1

HCID 866505643-(Pyrimidin-5-yloxy)-4,5-dihydroisoxazole

Procedure

3-(pyrimidin-5-yloxy)-4,5-dihydroisoxazole I-139a and I-139b was prepared in 3 steps from 4-butoxybenzaldehyde using Method 8 followed by cycloaddition using Method 1. The resulting bromo-4,5-dihydroisoxazole was reacted with 5-hydroxypyrimidine using Method 5. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=314.9 m/z. Activity: A

Workup

  1. customThese compounds can be separated

Sources & evidence

ORD record
ord-cf1212bc9584496e8775f6f1bf65c0c6
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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