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

HRID 1522295Notes

Reaction equation

HRID 1522295 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([NH2:28])=[N:10][CH:11]=[N:12][C:13]=2[O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[CH:5]=[CH:6][CH:7]=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>>[NH2:28][C:9]1[C:8]([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:7]=[CH:6][CH:5]=2)=[C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[N:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 22466617(E)-4-morpholinobut-2-enoic acidHCID 714740125-(3-Aminophenyl)-6-(4-phenoxyphenoxy)pyrimidin-4-amine

Product 1

HCID 71092933(E)-N-(3-(4-amino-6-(4-phenoxyphenoxy)pyrimidin-5-yl)phenyl)-4-morpholinobut-2-enamideYield 15%

Procedure

(E)-N-(3-(4-amino-6-(4-phenoxyphenoxy)pyrimidin-5-yl)phenyl)-4-morpholinobut-2-enamide was prepared from 5-(3-aminophenyl)-6-(4-phenoxyphenoxy)pyrimidin-4-amine and (E)-4-morpholinobut-2-enoic acid using Method E (15% yield). HPLC: 100%, RT=3.662 min. MS: m/z=524 [M+H]+, RT=3.66 min.

Sources & evidence

ORD record
ord-df247125f3ea48a69ca46de114c1c660
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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