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

HRID 1746129Notes

Reaction equation

HRID 1746129 reaction equation
C(OC1C=CC(C=O)=CC=1)(C)C.Br[C:14]1[CH2:18][CH2:17][O:16][N:15]=1.[OH:19][C:20]1[CH:21]=[N:22][CH:23]=[N:24][CH:25]=1>>[N:22]1[CH:21]=[C:20]([O:19][C:14]2[CH2:18][CH2:17][O:16][N:15]=2)[CH:25]=[N:24][CH:23]=1

Participants

4

Reactant 3

HCID 2500774-IsopropoxybenzaldehydeHCID 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-141a and I-141b were prepared in 3 steps from 4-iso-propoxybenzaldehyde 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]+=299.3 m/z. Activity: A

Workup

  1. customThese compounds can be separated

Sources & evidence

ORD record
ord-6a11d4710cfa40998a5d787302447e72
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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