(E)-4-morpholinobut-2-enoic acid → (E)-N-(3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)phenyl)-4-morpholinobut-2-enamide

HRID 1522294Notes

Reaction equation

HRID 1522294 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[O:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([NH2:12])[C:7]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.[O:29]1[CH2:34][CH2:33][N:32]([CH2:35]/[CH:36]=[CH:37]/[C:38](O)=[O:39])[CH2:31][CH2:30]1>>[NH2:12][C:8]1[N:9]=[CH:10][N:11]=[C:6]([O:5][C:4]2[CH:3]=[C:2]([NH:1][C:38](=[O:39])/[CH:37]=[CH:36]/[CH2:35][N:32]3[CH2:31][CH2:30][O:29][CH2:34][CH2:33]3)[CH:28]=[CH:27][CH:26]=2)[C:7]=1[C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 22466617(E)-4-morpholinobut-2-enoic acidHCID 867217356-(3-Aminophenoxy)-5-(4-phenoxyphenyl)pyrimidin-4-amine

Product 1

HCID 71092946(E)-N-(3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)phenyl)-4-morpholinobut-2-enamideYield 19%

Procedure

(E)-N-(3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)phenyl)-4-morpholinobut-2-enamide was prepared from 6-(3-aminophenoxy)-5-(4-phenoxyphenyl)pyrimidin-4-amine and (E)-4-morpholinobut-2-enoic acid using Method E (19% yield). HPLC: 100%, RT=3.605 min. MS: m/z=524 [M+H]+, RT=3.59 min.

Sources & evidence

ORD record
ord-1e2256319aad4b1a8c46dc8d1ed87be3
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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